Total Synthesis and Absolute Stereochemical Assignment of (+)- and (−)-Galbulimima Alkaloid 13

Mohammad Movassaghi,* Diana K. Hunt, and Meiliana Tjandra
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2006, 128 (25), pp 8126–8127
DOI: 10.1021/ja0626180
Publication Date (Web): June 1, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, movassag@mit.edu

Abstract

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We describe the total synthesis of (+)- and (−)-galbulimima alkaloid 13. The absolute stereochemistry of natural (−)-galbulimima alkaloid 13 is revised to 2S. Sequential use of catalytic cross-coupling and cross-metathesis reactions followed by an intramolecular Diels−Alder reaction provided the required trans-decalin AB-ring system and masked the C16 carbonyl as an N-vinyl carbamate for late-stage unveiling in the form of the necessary C16 enone. A vinyl radical cyclization secured the C-ring, while successful execution of our strategy for introduction of the CDE-ring system in complex galbulimima alkaloids provided the target pentacycle with complete diastereoselection.

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History

  • Published In Issue June 28, 2006
  • Received April 14, 2006

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