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Three-component coupling approach to trachyspic acid.

ABSTRACT: Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an ?,?-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

SUBMITTER: Schmitt DC

PROVIDER: S-EPMC3184321 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Three-component coupling approach to trachyspic acid.

Schmitt Daniel C DC Lam Leighann L Johnson Jeffrey S JS

Organic letters 20110831 19

Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an α,β-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means. ...[more]

PMID: 21879704

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