Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy

Authors

Errata

This article is corrected by:

  1. Errata: Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy Volume 48, Issue 45, 8396, Article first published online: 20 October 2009

  • We thank the National Institute of Health (GM13598) for their generous support of our program, and S. Lynch for assistance with NMR spectroscopy. J.D.S. thanks the American Cancer Society for a postdoctoral fellowship. We gratefully thank the Johnson Matthey Chemical Co. for donation of precious metal salts, and the Aldrich Chemical Co. for donation of (S,S)-8.

Abstract

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A triple-bond bonanza: The alkyne functional group can be a valuable handle for organic synthesis because the alkyne unit can function both as a nucleophile or as an electrophile when activated with an appropriate metal catalyst. This dual nature of the alkyne moiety has been exploitated for the concise total synthesis of the natural product soraphen A (see retrosynthesis; PMB=para-methoxybenzyl, TBS=tert-butyldimethylsilyl).

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