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Published August 19, 2011 | Accepted Version + Supplemental Material
Journal Article Open

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


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).

Attached Files

Accepted Version - nihms314306.pdf

Supplemental Material - ol2017615_si_001.cif

Supplemental Material - ol2017615_si_002.pdf

Supplemental Material - ol2017615_si_003.cif


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August 19, 2023
October 24, 2023