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Efficient synthesis of the 6,6-spiroacetal of spirofungin A

✍ Scribed by Takeshi Shimizu; Junichi Kusaka; Haruaki Ishiyama; Tadashi Nakata

Book ID: 104253858
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 121 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01184-5

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✦ Synopsis

The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps.

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