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

Handle URI:
http://hdl.handle.net/10754/597366
Title:
A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids
Authors:
Goldberg, Alexander F. G.; Stoltz, Brian M.
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.
Citation:
Goldberg AFG, Stoltz BM (2011) A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids. Organic Letters 13: 4474–4476. Available: http://dx.doi.org/10.1021/ol2017615.
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
KAUST Grant Number:
KUS-11-006-02
Issue Date:
19-Aug-2011
DOI:
10.1021/ol2017615
PubMed ID:
21786746
PubMed Central ID:
PMC3155617
Type:
Article
ISSN:
1523-7060; 1523-7052
Sponsors:
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 NTH-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).
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorGoldberg, Alexander F. G.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T12:31:43Zen
dc.date.available2016-02-25T12:31:43Zen
dc.date.issued2011-08-19en
dc.identifier.citationGoldberg AFG, Stoltz BM (2011) A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids. Organic Letters 13: 4474–4476. Available: http://dx.doi.org/10.1021/ol2017615.en
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.pmid21786746en
dc.identifier.doi10.1021/ol2017615en
dc.identifier.urihttp://hdl.handle.net/10754/597366en
dc.description.abstractA 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.en
dc.description.sponsorshipThis 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 NTH-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).en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleA Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloidsen
dc.typeArticleen
dc.identifier.journalOrganic Lettersen
dc.identifier.pmcidPMC3155617en
dc.contributor.institutionThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, USA.en
kaust.grant.numberKUS-11-006-02en
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