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

Alexander F. G. Goldberg, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

106 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)4474-4476
Number of pages3
JournalOrganic Letters
Volume13
Issue number16
DOIs
StatePublished - Aug 19 2011
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-11-006-02
Acknowledgements: 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).
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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