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  • Intramolecular silicon-assisted cross-coupling: total synthesis of (+)-brasilenyne.

Intramolecular silicon-assisted cross-coupling: total synthesis of (+)-brasilenyne.

Journal of the American Chemical Society (2002-12-19)
Scott E Denmark, Shyh-Ming Yang
초록

The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter and the successful application of the sequential ring closing metathesis/silicon-assisted intramolecular cross-coupling reaction for construction of the oxonin core structure of 1.

MATERIALS
제품 번호
브랜드
제품 설명

Sigma-Aldrich
Bis(trimethylsilyl)acetylene, 99%