CaltechAUTHORS
Published August 19, 2011 | Version Campus-Access Only
Journal Article Metadata-only

A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids

Creators

Abstract

A palladium-catalyzed (3 + 2) cycloaddition of a vinylcyclopropane and a β-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared in six steps from commercially available materials.

Additional Information

© 2011 American Chemical Society. Published In Issue August 19, 2011; Article ASAP July 25, 2011; Received: June 30, 2011. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS(R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. A.G. gratefully acknowledges the Natural Sciences and Engineering Research Council (NSERC) of Canada for a PGS D scholarship. Christopher Henry, Hosea Nelson, Kristy Tran, Florian Vogt, and Scott Virgil (Caltech) are thanked for helpful guidance. Lawrence Henling and Dr. Michael Day (Caltech) are gratefully acknowledged for X-ray crystallographic structural determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. The Varian 400 MHz NMR spectrometer was purchased via an NIH grant (RR027690).

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Additional details

Identifiers

PMCID
PMC3155617
Eprint ID
25300
DOI
10.1021/ol2017615
Resolver ID
CaltechAUTHORS:20110912-114011217

Funding

King Abdullah University of Science and Technology (KAUST)
KUS-11-006-02
Amgen
Abbott
Boehringer-Ingelheim
Caltech
Natural Sciences and Engineering Research Council of Canada (NSERC)
NSF
CHE-0639094
NIH
RR027690
NIH
R01GM080269-01

Dates

Created
2011-09-12
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field