Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

Alexander F.G. Goldberg, Robert A. Craig, Nicholas R. O'Connor, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Abstract A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodinus alkaloids.

Original languageEnglish
Article number45110
Pages (from-to)2983-2990
Number of pages8
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - 3 Jun 2015
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Ltd.

Funding

The authors wish to thank NIH-NIGMS ( R01GM080269-01 ), Amgen, and Caltech for financial support. A.F.G.G. thanks the Natural Sciences and Engineering Research Council (NSERC) of Canada for a PGS D scholarship. R.A.C. gratefully acknowledges the support of this work provided by a fellowship from the National Cancer Institute of the National Institutes of Health under Award Number F31CA174359.

FundersFunder number
NIH-NIGMSR01GM080269-01
National Institutes of HealthF31CA174359
National Cancer Institute
Amgen
Natural Sciences and Engineering Research Council of Canada

    Keywords

    • Claisen rearrangement
    • Cycloaddition
    • Cyclopropanes
    • Melodinus alkaloids
    • Stereoselective synthesis

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