View Item 

Show simple item record

Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods

dc.contributor.authorKhatri, Hem Raj
dc.contributor.authorCarney, Nolan
dc.contributor.authorRutkoski, Ryan
dc.contributor.authorBhattarai, Bijay
dc.contributor.authorNagorny, Pavel
dc.date.accessioned2020-03-17T18:34:39Z
dc.date.availableWITHHELD_12_MONTHS
dc.date.available2020-03-17T18:34:39Z
dc.date.issued2020-02-21
dc.identifier.citationKhatri, Hem Raj; Carney, Nolan; Rutkoski, Ryan; Bhattarai, Bijay; Nagorny, Pavel (2020). "Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods." European Journal of Organic Chemistry 2020(7): 755-776.
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.urihttps://hdl.handle.net/2027.42/154510
dc.publisherWiley‐VCH
dc.subject.otherTerpenoids
dc.subject.otherTotal synthesis
dc.subject.otherCatalysis
dc.subject.otherSteroids
dc.subject.otherSynthetic methods
dc.titleRecent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/154510/1/ejoc201901466_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/154510/2/ejoc201901466.pdf
dc.identifier.doi10.1002/ejoc.201901466
dc.identifier.sourceEuropean Journal of Organic Chemistry
dc.identifier.citedreferencea) H. R. Khatri, B. Bhattarai, W. Kaplan, Z. Li, M. J. C. Long, Y. Aye and P. Nagorny, J. Am. Chem. Soc, 2019, 141, 4849; b) J.‐H. Tay, V. Dorokhov, S. Wang and P. Nagorny, J. Antibiot, 2019, 72, 437; c) J. Lee, S. Wang, M. Callahan and P. Nagorny, Org. Lett, 2018, 20, 2067; d) B. Bhattarai and P. Nagorny, Org. Lett, 2018, 20, 154; e) W. Kaplan, H. R. Khatri and P. Nagorny, J. Am. Chem. Soc, 2016, 138, 7194; f) P. Nagorny and N. Cichowicz, Strategies and Tactics Org. Synthesis, 2016, 48, 237; g) N. Cichowicz, W. Kaplan, I. Khomutnyk, B. Bhattarai, Z. Sun and P. Nagorny, J. Am. Chem. Soc, 2015, 137, 14341.
dc.identifier.citedreferencea) S. Isayama and T. Mukaiyama, Chem. Lett, 1989, 18, 1071; b) T. Mukaiyama, S. Isayama, S. Inoki, K. Kato, T. Yamada and T. Takai, Chem. Lett, 1989, 18, 449; c) I. Isayama and T. Mukaiyama, Chem. Lett, 1989, 18, 569; d) S. Isayama and T. Mukaiyama, Chem. Lett, 1989, 18, 573.
dc.identifier.citedreferenceS. W. M. Crossley, C. Obradors, R. M. Martinez and R. A. Shenvi, Chem. Rev, 2016, 116, 8912.
dc.identifier.citedreferencea) J. Shi, G. Manolikakes, C.‐H. Yeh, C. A. Guerrero, R. A. Shenvi, H. Shigehisa and P. S. Baran, J. Am. Chem. Soc, 2011, 133, 8014; b) R. A. Shenvi, C. A. Guerrero, J. Shi, C.‐C. Li and P. S. Baran, J. Am. Chem. Soc, 2008, 130, 7241.
dc.identifier.citedreferencea) H. Renata, Q. Zhou, G. Dunstl, J. Felding, R. R. Merchant, C.‐H. Yeh and P. S. Baran, J. Am. Chem. Soc, 2015, 137, 1330; b) H. Renata, Q. Zhou and P. S. Baran, Science, 2013, 339, 59.
dc.identifier.citedreferenceD. Zhu and B. Yu, J. Am. Chem. Soc, 2015, 137, 15098.
dc.identifier.citedreferencea) J. C. Lo, D. Kim, C.‐M. Pan, J. T. Edwards, Y. Yabe, J. Gui, T. Qin, S. Gutierrez, J. Giacoboni, M. W. Smith, P. L. Holland and P. S. Baran, J. Am. Chem. Soc, 2017, 139, 2484; b) J. C. Lo, J. Gui, Y. Yabe, C.‐M. Pan and P. S. Baran, Nature 2014, 505‐516, 343.
dc.identifier.citedreferenceD. T. George, E. J. Kuenstner, S. V. Pronin, J. Am. Chem. Soc. 2015, 137, 15410.
dc.identifier.citedreferenceS. D. Holmbo, N. A. Godfrey, J. J. Hirner and S. V. Pronin, J. Am. Chem. Soc, 2016, 138, 12316.
dc.identifier.citedreferenceY. Y. See, A. T. Herrmann, Y. Aihara and P. S. Baran, J. Am. Chem. Soc, 2015, 137, 13776.
dc.identifier.citedreferencea) B. Schonecker, C. Lange, T. Zheldakova, W. Gunther, H. Gorls and G. Vaughan, Tetrahedron, 2005, 61, 103; b) B. Schonecker, T. Zheldakova, C. Lange, W. Gunther, H. Gorls and M. Bohl, Chem. Eur. J, 2004, 10, 6029; c) B. Schönecker, T. Zheldakova, Y. Liu, M. Kotteritzsch, W. Gunther and H. Gorls, Angew. Chem. Int. Ed, 2003, 42, 3240; Angew. Chem, 2003, 115, 3361.
dc.identifier.citedreferenceH. T. Dao and P. S. Baran, Angew. Chem. Int. Ed, 2014, 53, 14382; Angew. Chem, 2014, 126, 14610.
dc.identifier.citedreferenceK. Sakata, Y. Wang, D. Urabe and M. Inoue, Org. Lett, 2018, 20, 130.
dc.identifier.citedreferencea) T. Tokuyama, J. Daly and B. Witkop, J. Am. Chem. Soc, 1969, 91, 3931; b) T. Tokuyama, J. Daly, B. Witkop, I. L. Karle and J. Karle, J. Am. Chem. Soc, 1968, 90, 1917.
dc.identifier.citedreferencea) M. Kurosu, L. R. Marcin, T. J. Grinsteiner and Y. Kishi, J. Am. Chem. Soc, 1998, 120, 6627; b) R. Imhof, E. Gossinger, W. Graf, H. Berner, L. Berner‐Fenz and H. Wehrli, Helv. Chim. Acta, 1972, 55, 1151; c) R. Imhof, E. Gossinger, W. Graf, L. Berner‐Fenz, H. Berner, R. Schaufelberger and H. Wehrli, Helv. Chim. Acta, 1973, 56, 139.
dc.identifier.citedreferencea) H. Fujino, M. Nagatomo, A. Paudel, S. Panthee, H. Hamamoto, K. Sekimizu and M. Inoue, Angew. Chem. Int. Ed, 2017, 56, 11865; Angew. Chem, 2017, 129, 12027; b) S. Matsumura, Y. Matsui, M. Nagatomo and M. Inoue, Tetrahedron, 2016, 72, 4859; c) M. Nagatomo, H. Nishiyama, H. Fujino and M. Inoue, Angew. Chem. Int. Ed, 2015, 54, 1537; Angew. Chem, 2015, 127, 1557; d) M. Nagatomo, D. Kamimura, Y. Matsui, K. Masuda and M. Inoue, Chem. Sci, 2015, 6, 2765.
dc.identifier.citedreferenceL. K. G. Ackerman, M. M. Lovell and D. J. Weix, Nature, 2015, 524, 454.
dc.identifier.citedreferencea) M. S. Reddy, H. Zhang, S. Phoenix and P. Deslongchamps, Chem. Asian J, 2009, 4, 725; b) H. Zhang, M. S. Reddy, S. Phoenix and P. Deslongchamps, Angew. Chem. Int. Ed, 2008, 47, 1272; Angew. Chem, 2008, 120, 1292.
dc.identifier.citedreferencea) D. Urabe, Y. Nakagawa, K. Mukai, K. Fukushima, N. Aoki, H. Itoh, M. Nagatomo and M. Inoue, J. Org. Chem, 2018, 83, 13888; b) K. Mukai, S. Kasuya, Y. Nakagawa, D. Urabe and M. Inoue, Chem. Sci, 2015, 6, 3383; c) K. Mukai, D. Urabe, S. Kasuya, N. Aoki and M. Inoue, Angew. Chem. Int. Ed, 2013, 52, 5300; Angew. Chem, 2013, 125, 5408.
dc.identifier.citedreferencea) Z. G. Hajos, D. R. Parrish, German Patent DE 2102623, July 29, 1971; b) Z. G. Hajos and D. R. Parrish, J. Org. Chem, 1974, 39, 1615; c) U. Eder, G. Sauer, R. Wiechert, German Patent DE 2014757, Oct 7, 1971; d) U. Eder, G. Sauer and R. Wiechert, Angew. Chem. Int. Ed. Engl, 1971, 10, 496; Angew. Chem, 1971, 83, 492.
dc.identifier.citedreferenceY. Hayashi, S. Koshino, K. Ojima and E. Kwon, Angew. Chem. Int. Ed, 2017, 56, 11812; Angew. Chem, 2017, 129, 11974.
dc.identifier.citedreferenceD.‐H. Jhuo, B.‐C. Hong, C.‐W. Chang and G.‐H. Lee, Org. Lett, 2014, 16, 2724.
dc.identifier.citedreferenceS. Prévost, N. Dupre, M. Leutzsch, Q. Wang, V. Wakchaure and B. List, Angew. Chem. Int. Ed, 2014, 53, 8770; Angew. Chem, 2014, 126, 8915.
dc.identifier.citedreferenceY. Hayashi, Chem. Sci, 2016, 7, 866.
dc.identifier.citedreferencea) M. Marigo, T. C. Wabnitz, D. Fielenbach and K. A. Joergensen, Angew. Chem. Int. Ed, 2005, 44, 794; Angew. Chem, 2005, 117, 804; b) Y. Hayashi, H. Gotoh, T. Hayashi and M. Shoji, Angew. Chem. Int. Ed, 2005, 44, 4212; Angew. Chem, 2005, 117, 4284.
dc.identifier.citedreferenceS. N. Ananchenko and I. V. Torgov, Tetrahedron Lett, 1963, 4, 1553.
dc.identifier.citedreferencea) V. S. Enev, J. Mohr, M. Harre and K. Nickisch, Tetrahedron: Asymmetry, 1998, 9, 2693; b) M. Braun, R. Fleischer, B. Mai, M.‐A. Schneider and S. Lachenicht, Adv. Synth. Catal, 2004, 346, 474 For other asymmetric syntheses of the Torgov diene: c) G. Quinkert, M. Del Grosso, A. Bucher, M. Bauch, W. Dcring, J. W. Bats and G. Drner, Tetrahedron Lett, 1992, 33, 3617; d) K. Tanaka, H. Nakashima, T. Taniguchi and K. Ogasawara, Org. Lett, 2000, 2, 1915; e) Y.‐Y. Yeung, R.‐J. Chein and E. J. Corey, J. Am. Chem. Soc, 2007, 129, 10346; f) D. Soorukram and P. Knochel, Org. Lett, 2007, 9, 1021; g) E. Canales and E. J. Corey, Org. Lett, 2008, 10, 3271.
dc.identifier.citedreferenceT. James, M. van Gemmeren and B. List, Chem. Rev, 2015, 115, 9388.
dc.identifier.citedreferenceY.‐Y. Yeung, R.‐J. Chein and E. J. Corey, J. Am. Chem. Soc, 2007, 129, 10346.
dc.identifier.citedreferenceE. J. Corey, B. Czako and L. Kurti, in: Molecules and Medicine, Hoboken, NJ: Wiley‐VCH 2007
dc.identifier.citedreferencea) J. Feng, M. Holmes and M. J. Krische, Chem. Rev, 2017, 117, 12564; b) E. A. Peterson and L. E. Overman, Proc. Natl. Acad. Sci. USA, 2004, 101, 11943; c) M. Buschleb, S. Dorich, S. Hanessian, D. Tao, K. B. Schenthal and L. E. Overman, Angew. Chem. Int. Ed, 2016, 55, 4156; Angew. Chem, 2016, 128, 4226.
dc.identifier.citedreferencea) N. A. Burns, P. S. Baran and R. W. Hoffmann, Angew. Chem. Int. Ed, 2009, 48, 2854; Angew. Chem, 2009, 121, 2896; b) T. Newhouse, P. S. Baran and R. W. Hoffmann, Chem. Soc. Rev, 2009, 38, 3010.
dc.identifier.citedreferencea) J. W. Lehmann, D. J. Blair and M. D. Burke, Nat. Rev. Chem, 2018, 2, 0115; b) J.‐L. Shih, P.‐A. Chen and J. A. May, Beilstein J. Org. Chem, 2016, 12, 985; c) R. Ardkhean, D. F. J. Caputo, S. M. Morrow, H. Shi, Y. Xiong and E. A. Anderson, Chem. Soc. Rev, 2016, 45, 1557.
dc.identifier.citedreferenceSelected reviews related to the synthesis of steroids: a) M. T. C. Pessoa, L. A. Barbosa and J. A. F. P. Villar, Stud. Nat. Prod. Chem, 2018, 57, 79; b) H. Mizoguchi, J. Synth. Org. Chem. Jpn, 2017, 75, 253; c) M. Michalak, K. Michalak and J. Wicha, Nat. Prod. Rep, 2017, 34, 361; d) P. Gupta and G. Panda, Eur. J. Org. Chem, 2014, 8004; e) R. Singh and G. Panda, Tetrahedron, 2013, 69, 2853; f) B. Heasley, Chem. Eur. J, 2012, 18, 3092; g) M. Kotora, F. Hessler and B. Eignerova, Eur. J. Org. Chem, 2012, 2012, 29; h) J. R. Hanson, Nat. Prod. Rep, 2010, 27, 887; i) D. F. Covey, Steroids, 2009, 74, 577; j) J. Wolfling, ARKIVOC, 2007, 210; k) M. Ibrahim‐Quali, Steroids, 2008, 73, 375; l) M. Ibrahim‐Quali, Steroids, 2007, 72, 475; m) M. Ibrahim‐Quali and M. Santelli, Steroids, 2006, 71, 1025; n) A. S. Chapelon, D. Moraléda, R. Rodriguez, C. Ollivier and M. Santelli, Tetrahedron, 2007, 63, 11511; o) L. F. Tietze, H. P. Bell and S. Chandrasekhar, Angew. Chem. Int. Ed, 2003, 42, 3996; Angew. Chem, 2003, 115, 4128; p) R. Skoda‐Foldes and L. Kollar, Chem. Rev, 2003, 103, 4095; q) J. F. Biellmann, Chem. Rev, 2003, 103, 2019; r) G. Mehta and V. Singh, Chem. Soc. Rev, 2002, 31, 324.
dc.identifier.citedreferenceFor the selected reviews on the synthesis of terpenoids refer to: a) K. Hung, X. Hu and T. J. Maimone, Nat. Prod. Rep, 2018, 35, 174; b) Y. Zou and A. B. Smith III, J. Antibiot, 2018, 71, 185; c) Z. G. Brill, M. L. Condakes, C. P. Ting and T. J. Maimone, Chem. Rev, 2017, 117, 11753; d) M. A. Corsello, J. Kim and N. K. Garg, Chem. Sci, 2017, 8, 5836; e) J. E. Zweig, D. E. Kim and T. R. Newhouse, Chem. Rev, 2017, 117, 11680; f) C. N. Ungarean, E. H. Southgate and D. Sarlah, Org. Biomol. Chem, 2016, 14, 5454; g) D. Urabe, T. Asaba and M. Inoue, Chem. Rev, 2015, 115, 9207; h) P. S. Riehl, Y. C. DePorre, A. M. Armaly, E. J. Groso and C. S. Schindler, Tetrahedron, 2015, 71, 6629; i) T. Yoshimura, Tetrahedron Lett, 2014, 55, 5109; j) E. C. Cherney and P. S. Baran, Isr. J. Chem, 2011, 51, 391.
dc.identifier.citedreferenceFor the selected examples of the studies in the area of steroid total synthesis published since 2014 and not covered in this review refer to: a) Y. Wang, W. Ju, H. Tian, S. Sun, X. Li, W. Tian and J. Gui, J. Am. Chem. Soc, 2019, 141, 5021; b) R. C. Heinze and P. Heretsch, J. Am. Chem. Soc, 2019, 141, 1222; c) D. E. Kim, J. E. Zweig and T. R. Newhouse, J. Am. Chem. Soc, 2019, 141, 1479; d) A. Nagata, Y. Akagi, S. S. Masoud, M. Yamanaka, A. Kittaka, M. Uesugi, M. Odagi and K. Nagasawa, J. Org. Chem, 2019, 84, 7630; e) Y. Zou, X. Li, Y. Yang, S. Berrit, J. Melvin, S. Gonzales, M. Spafford and A. S. Smith III, J. Am. Chem. Soc, 2018, 140, 9502; f) J. Liu, J. Wu, J.‐H. Fan, X. Yan, G. Mei and C.‐C. Li, J. Am. Chem. Soc, 2018, 140, 5365; g) Y. Wang, W. Ju, H. Tian, W. Tian and J. Gui, J. Am. Chem. Soc, 2018, 140, 9413; h) J. Danielsson, D. X. Sun, X.‐Y. Chen, A. L. Risinger, S. L. Mooberry and E. J. Sorensen, Org. Lett, 2017, 19, 4892; i) G. Xu, M. Elkin, D. Tantillo, T. R. Newhouse and T. Maimone, Angew. Chem. Int. Ed, 2017, 56, 12498; Angew. Chem, 2017, 129, 12672; j) A. Nakazaki, K. Hashimoto, A. Ikeda, T. Shibata and T. Nishikawa, J. Org. Chem, 2017, 82, 9097; k) M. M. Logan, T. Toma, R. Thomas‐Tran and J. Du Bois, Science, 2016, 354, 865; l) R. J. Sharpe and J. S. Johnson, J. Am. Chem. Soc. 2015, 137, 4968; m) A. M. Camelio, T. C. Johnson and D. Siegel, J. Am. Chem. Soc, 2015, 137, 11864.
dc.identifier.citedreferenceK. Du, P. Guo, Y. Chen, Z. Cao, Z. Wang and W. Tang, Angew. Chem. Int. Ed, 2015, 54, 3033; Angew. Chem, 2015, 127, 3076.
dc.identifier.citedreferencea) T. J. Maimone and P. S. Baran, Nat. Chem. Biol, 2007, 3, 12; b) J. Gershenzon and N. Dudareva, Nat. Chem. Biol, 2007, 3, 408; c) R. A. Yoder and J. N. Johnston, Chem. Rev, 2005, 105, 4730.
dc.identifier.citedreferencea) M. Mori, K. Chiba and Y. Ban, Tetrahedron Lett, 1977, 18, 1037; b) Y. Sato, M. Soeoka and M. Shibasaki, J. Org. Chem, 1989, 54, 4738; c) N. E. Carpenter, D. J. Kucera and L. E. Overman, J. Org. Chem, 1989, 54, 5846; d) A. B. Dounay and L. E. Overman, Chem. Rev, 2003, 103, 2945; e) S. P. Maddaford, N. G. Andersen, W. A. Cristofoli and B. A. Keay, J. Am. Chem. Soc, 1996, 118, 10766.
dc.identifier.citedreferenceFor overview of this topic, see: a) A. R. Pape, K. P. Kaliappan and E. P. Kundig, Chem. Rev, 2000, 100, 2917; b) S. Quideau, L. Pouys_gu and D. Deffieux, Synlett, 2008, 467; c) L. Pouys_gu, D. Deffieux and S. Quideau, Tetrahedron, 2010, 66, 2235; d) L. Pouys_gu, T. Sylla, T. Garnier, L. B. Rojas, J. Charris, D. Deffieux and S. Quideau, Tetrahedron, 2010, 66, 5908; e) S. P. Roche and J. A. Porco Jr, Angew. Chem. Int. Ed, 2011, 50, 4068; Angew. Chem, 2011, 123, 4154; f) C.‐X. Zhuo, W. Zhang and S.‐L. You, Angew. Chem. Int. Ed, 2012, 51, 12662; Angew. Chem, 2012, 124, 12834; g) Q. Ding, Y. Ye and R. Fan, Synthesis, 2013, 45, 1.
dc.identifier.citedreferenceS. Rousseaux, J. Garcia‐Fortanet, M. A. D. Aguela Sanchez and S. L. Buchwald, J. Am. Chem. Soc, 2011, 133, 9282.
dc.identifier.citedreferenceM. Del Bel, A. R. Abela, J. D. Ng and C. A. Guerrero, J. Am. Chem. Soc, 2017, 139, 6819.
dc.identifier.citedreferenceP. W. Brian and J. C. McGowan, Nature, 1945, 156, 144.
dc.identifier.citedreferenceJ. S. Moffatt, J. D. Bu’Lock and T. H. Yuen, J. Chem. Soc., D, 1969, 839.
dc.identifier.citedreferenceE. A. Anderson, E. J. Alexanian and E. J. Sorensen, Angew. Chem. Int. Ed, 2004, 43, 1998; Angew. Chem, 2004, 116, 2032.
dc.identifier.citedreferenceA. Fürstner, O. Thiel and G. Blanda, Org. Lett, 2000, 2, 3731.
dc.identifier.citedreferenceW. A. Cristofoli and B. A. Keay, Synlett, 1994, 625.
dc.identifier.citedreferenceR. Wittenberg, J. Srogl, M. Egi and L. S. Liebeskind, Org. Lett, 2003, 5, 3033.
dc.identifier.citedreferencea) W. S. Kim, Z. A. Shalit, S. Nguyen, E. Schoepke, A. Eastman, T. P. Burris, A. B. Gaur and G. C. Micalizio, Nat. Commun, 2019, 10, 2448; b) H. T. Wai, K. Du, J. Anesini, W. S. Kim, A. Eastman and G. C. Micalizio, Org. Lett, 2018, 20, 6220; c) W. S. Kim, K. Du, A. Eastman, R. P. Hughes and G. C. Micalizio, Nat. Chem, 2017, 10, 70.
dc.identifier.citedreferencea) H. A. Reichard, M. McLaughlin, M. Z. Chen and G. C. Micalizio, Eur. J. Org. Chem, 2010, 2010, 391; b) H. A. Reichard and G. C. Micalizio, Chem. Sci, 2011, 2, 573; c) G. C. Micalizio and H. Mizoguchi, Isr. J. Chem, 2017, 57, 228.
dc.identifier.citedreferenceJ. Ryan and G. C. Micalizio, J. Am. Chem. Soc, 2006, 128, 2764.
dc.identifier.citedreferencea) T. Sasaki, S. Eguchi and T. Kiriyama, J. Org. Chem, 1973, 38, 2230; b) R. L. Danheiser, J. M. Morin Jr, M. Yu and A. Basak, Tetrahedron Lett, 1981, 22, 4205; c) P. G. Gassman, L. Tan and T. R. Hoye, Tetrahedron Lett, 1996, 37, 439; d) M. G. Banwell, J. E. Harvey, D. C. R. Hockless and A. W. Wu, J. Org. Chem, 2000, 65, 4241.
dc.identifier.citedreferencea) G. A. Olah and J. M. Bollinger, J. Am. Chem. Soc, 1968, 90, 6082; b) C. D. Poulter and S. Winstein, J. Am. Chem. Soc, 1969, 91, 3649; c) C. D. Poulter and S. Winstein, J. Am. Chem. Soc, 1969, 91, 3650; d) T. S. Sorensen and K. Ranganayakulu, Tetrahedron Lett, 1970, 11, 659.
dc.identifier.citedreferencea) S. Seko, Y. Tanabe and G. Suzukamo, Tetrahedron Lett, 1990, 31, 6883; b) Y. Tanabe, et al., J. Chem. Soc., Perkin Trans. 1, 1996, 2157.
dc.identifier.citedreferenceW. S. Kim, C. Aquino, H. Mizoguchi and G. C. Micalizio, Tetrahedron Lett, 2015, 56, 3557.
dc.identifier.citedreferencea) H. Ishibashi, K. Ishihara and H. Yamamoto, J. Am. Chem. Soc, 2004, 126, 11122; b) K. Ishihara, H. Ishibashi and H. Yamamoto, J. Am. Chem. Soc, 2001, 123, 1505; c) K. Ishihara, S. Nakamura and H. Yamamoto, J. Am. Chem. Soc, 1999, 121, 4906.
dc.identifier.citedreferenceK. Surendra and E. J. Corey, J. Am. Chem. Soc, 2012, 134, 11992.
dc.identifier.citedreferenceJ. Xie, J. Wang and G. Dong, Org. Lett, 2017, 19, 3017.
dc.identifier.citedreferenceM. Grigalunas, T. Anker, P.‐O. Norrby, O. Wiest and P. Helquist, Org. Lett, 2014, 16, 397.
dc.identifier.citedreferenceZ. Lu, X. Zhang, Z. Guo, Y. Chen, T. Mu and A. Li, J. Am. Chem. Soc, 2018, 140, 9211.
dc.identifier.citedreferenceN. A. Godfrey, D. J. Schatz and S. V. Pronin, J. Am. Chem. Soc, 2018, 140, 12770.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
ejoc201901466_am.pdf
Size:
1.289MB
Format:
PDF
View/Open
Name:
ejoc201901466.pdf
Size:
5.624MB
Format:
PDF
View/Open

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.