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A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.

ABSTRACT: A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2).

SUBMITTER: Smith AB

PROVIDER: S-EPMC514431 | biostudies-other | 2004 Aug

REPOSITORIES: biostudies-other

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A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.

Smith Amos B AB Adams Christopher M CM Barbosa Stephanie A Lodise SA Degnan Andrew P AP

Proceedings of the National Academy of Sciences of the United States of America 20040526 33

A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2). ...[more]

PMID: 15163795

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