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Stereoselective synthesis of the C10C24 fragment of FK-506

✍ Scribed by Zhaoyin Wang

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 267 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)70631-9

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✦ Synopsis

A highly stereoselective route to the CIO-CZ~ fragment of FK-506 is described.

Recently

the potent immunosuppressant FK-506 was isolated from Streptomyces tsukuaensis and its structure was assigned as the novel 23-membered macrocyclic lactone 1.1 The activity of this unique macrolide is reported to be considerably greater than cyclosporin A itself, which is currently used in clinical organ transplants. The exceptional biological activity of FK-506 has lead to extensive studies,* and the first total synthesis was recently achieved by the scientists of Merck Sharp & Dohme.3 In this communication, a synthesis of a protected Clo-C24 fragment 2 of FK-506 is reported that uses a stereoselective alkylation reaction as the key step.

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