Enantioselective Total Synthesis of FD-891

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-met...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-03, Vol.128 (10), p.3128-3129
Main Authors: Crimmins, Michael T, Caussanel, Franck
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Chemistry
Exact sciences and technology
General aspects
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Macrolides - chemical synthesis
Medical sciences
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Stereoisomerism
Streptomyces - chemistry
Streptomyces - metabolism
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja060018v