Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers
dc.contributor.author | Rej, RK | |
dc.contributor.author | Nanda, S | |
dc.date.accessioned | 2023-09-13T13:20:09Z | |
dc.date.available | 2023-09-13T13:20:09Z | |
dc.date.issued | 2014-02-01 | |
dc.identifier.issn | 1434-193X | |
dc.identifier.issn | 1099-0690 | |
dc.identifier.uri | https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000336261500020&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=cc40378bfc9614a14500fbd6db90869f | |
dc.identifier.uri | https://hdl.handle.net/2027.42/177670 | en |
dc.description.abstract | Chemoenzymatic asymmetric total synthesis of the (Z)-isomer of the naturally occurring decanolide cytospolides D, E and six stereoisomers is reported. The main highlight of the synthetic venture involves ring-closing metathesis (RCM) reaction of a suitably functionalized ester compound, which was assembled by the Yamaguchi coupling of the required acid and alcohol fragments. The alcohol fragment was ac- cessed by two alternative chemoenzymatic processes, one being hydroxynitrile lyase mediated hydrocyanation, whereas lipase-catalyzed transesterification was the key sep in the second route. The acid fragment was constructed by an enantioselective enzymatic desymmetrization (EED) of prochiral 2-methyl-1,3-propanediol and Corey-Bakshi-Shibata (CBS) mediated stereoselective carbonyl reduction. | |
dc.language | en | |
dc.publisher | Wiley | |
dc.subject | Natural products | |
dc.subject | Asymmetric synthesis | |
dc.subject | Hydrocyanation | |
dc.subject | Ring closing metathesis | |
dc.subject | Chiral resolution | |
dc.subject | Enzymes | |
dc.subject | Enantioselectivity | |
dc.title | Chemoenzymatic asymmetric total synthesis of nonanolide (Z)-cytospolides D, E and their stereoisomers | |
dc.type | Article | |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/177670/2/Eur J Org Chem - 2013 - Rej.pdf | |
dc.identifier.doi | 10.1002/ejoc.201301365 | |
dc.identifier.doi | https://dx.doi.org/10.7302/8127 | |
dc.identifier.source | European Journal of Organic Chemistry | |
dc.description.version | Published version | |
dc.date.updated | 2023-09-13T13:20:08Z | |
dc.identifier.orcid | 0000-0003-0904-9137 | |
dc.identifier.volume | 2014 | |
dc.identifier.issue | 4 | |
dc.identifier.startpage | 860 | |
dc.identifier.endpage | 871 | |
dc.identifier.name-orcid | Rej, RK; 0000-0003-0904-9137 | |
dc.identifier.name-orcid | Nanda, S | |
dc.working.doi | 10.7302/8127 | en |
dc.owningcollname | Internal Medicine, Department of |
Files in this item
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.