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Total synthesis of apoptolidin A.

ABSTRACT: A highly convergent, enantioselective total synthesis of the potent antitumor agent apoptolidin A has been completed. The key transformations include highly selective glycosylations to attach the C27 disaccharide and the C9 6'-deoxy-l-glucose, a cross-metathesis to incorporate the C1-C10 trienoate unit, and a Yamaguchi macrolactonization to complete the macrocycle. Twelve stereocenters in the polypropionate segments and sugar units were established through diastereoselective chlorotitanium enolate aldol reactions.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2653204 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Total synthesis of apoptolidin A.

Crimmins Michael T MT Christie Hamish S HS Long Alan A Chaudhary Kleem K

Organic letters 20090201 4

A highly convergent, enantioselective total synthesis of the potent antitumor agent apoptolidin A has been completed. The key transformations include highly selective glycosylations to attach the C27 disaccharide and the C9 6'-deoxy-l-glucose, a cross-metathesis to incorporate the C1-C10 trienoate unit, and a Yamaguchi macrolactonization to complete the macrocycle. Twelve stereocenters in the polypropionate segments and sugar units were established through diastereoselective chlorotitanium enola ...[more]

PMID: 19199767

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