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

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

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.

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製品内容

Sigma-Aldrich
ビス(トリメチルシリル)アセチレン, 99%