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Enantioselective total synthesis of FD-891.

ABSTRACT: The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

SUBMITTER: Crimmins MT

PROVIDER: S-EPMC2546579 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of FD-891.

Crimmins Michael T MT Caussanel Franck F

Journal of the American Chemical Society 20060301 10

The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits. ...[more]

PMID: 16522077

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