Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction

SE Denmark, SM Yang

Index: Denmark, Scott E.; Yang, Shyh-Ming Journal of the American Chemical Society, 2004 , vol. 126, # 39 p. 12432 - 12440

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Citation Number: 99

Abstract

The first enantioselective total synthesis of (+)-brasilenyne (1) has been achieved in 19 linear steps, with 5.1% overall yield from l-(S)-malic acid. The construction of the oxonin core containing a 1, 3-cis, cis diene unit was accomplished with a tandem ring-closing metathesis/silicon-assisted intramolecular cross-coupling reaction. In addition, a key propargylic stereogenic center was created through a novel, highly diastereoselective ring ...