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Total Synthesis of the Diterpenoid (+)â Harringtonolide
dc.contributor.authorZhang, Hai‐jun
dc.contributor.authorHu, Lin
dc.contributor.authorMa, Zhiqiang
dc.contributor.authorLi, Ruining
dc.contributor.authorZhang, Zhen
dc.contributor.authorTao, Cheng
dc.contributor.authorCheng, Bin
dc.contributor.authorLi, Yun
dc.contributor.authorWang, Huifei
dc.contributor.authorZhai, Hongbin
dc.date.accessioned2017-06-16T20:09:44Z
dc.date.available2017-11-01T15:31:30Zen
dc.date.issued2016-09-12
dc.identifier.citationZhang, Hai‐jun ; Hu, Lin; Ma, Zhiqiang; Li, Ruining; Zhang, Zhen; Tao, Cheng; Cheng, Bin; Li, Yun; Wang, Huifei; Zhai, Hongbin (2016). "Total Synthesis of the Diterpenoid (+)â Harringtonolide." Angewandte Chemie International Edition 55(38): 11638-11641.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/137303
dc.description.abstractDescribed herein is the first asymmetric total synthesis of (+)â harringtonolide, a natural diterpenoid with an unusual tropone imbedded in a cagelike framework. The key transformations include an intramolecular Dielsâ Alder reaction and a rhodiumâ complexâ catalyzed intramolecular [3+2] cycloaddition to install the tetracyclic core as well as a highly efficient tropone formation.Ever more rings: The first asymmetric total synthesis of the diterpenoid (+)â harringtonolide is described. The key features include an asymmetric transfer hydrogenation, an intramolecular Dielsâ Alder reaction, chemoselective functionalization of an olefin in the presence of an acetylenic group, a rhodiumâ catalyzed intramolecular [3+2] cycloaddition, and efficient formation of the tropone.
dc.publisherWiley Periodicals, Inc.
dc.subject.othertotal synthesis
dc.subject.otherterpenoids
dc.subject.othernatural products
dc.subject.othercycloaddition
dc.subject.otherasymmetric synthesis
dc.titleTotal Synthesis of the Diterpenoid (+)â Harringtonolide
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137303/1/anie201605879-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137303/2/anie201605879_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137303/3/anie201605879.pdf
dc.identifier.doi10.1002/anie.201605879
dc.identifier.sourceAngewandte Chemie International Edition
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