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Enantioselective Total Synthesis of (+)-Psiguadial B

Chapman, Lauren M. and Beck, Jordan C. and Wu, Linglin and Reisman, Sarah E. (2016) Enantioselective Total Synthesis of (+)-Psiguadial B. Journal of the American Chemical Society, 138 (31). pp. 9803-9806. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20160815-142455841

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Abstract

The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp^3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.6b07229DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jacs.6b07229PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.6b07229Related ItemSupporting Information
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2016 American Chemical Society. Received: July 13, 2016. Published: July 24, 2016. Prof. Greg Fu is gratefully acknowledged for insightful discussions. We thank Dr. Allen Oliver and Dr. Nathan Schley for X-ray crystallographic structure determination, Dr. David VanderVelde for assistance with NMR structure determination, Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Materia, Inc. for a donation of HG-II catalyst. Fellowship support was provided by the NSF (L.M.C., Grant DGE-1144469) and SNF (L.W., Grant PBZHP2-147311). S.E.R. is an American Cancer Society Research Scholar and a Heritage Medical Research Foundation Investigator. Financial support from the California Institute of Technology, the NSF (CHE 1057143), the American Cancer Society, the Research Corporation Cottrell Scholars Program, and DuPont is gratefully acknowledged.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Swiss National Fund (SNF)PBZHP2-147311
NSFCHE-1057143
American Cancer SocietyUNSPECIFIED
Cottrell Scholar of Research CorporationUNSPECIFIED
Heritage Medical Research FoundationUNSPECIFIED
CaltechUNSPECIFIED
DuPontUNSPECIFIED
Record Number:CaltechAUTHORS:20160815-142455841
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160815-142455841
Official Citation:Enantioselective Total Synthesis of (+)-Psiguadial B Lauren M. Chapman, Jordan C. Beck, Linglin Wu, and Sarah E. Reisman Journal of the American Chemical Society 2016 138 (31), 9803-9806 DOI: 10.1021/jacs.6b07229
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:69632
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Aug 2016 22:15
Last Modified:31 Mar 2017 19:24

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