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An enantioselective synthesis of the C1C9 segment of antitumor macrolide peloruside A

✍ Scribed by Arun K. Ghosh; Jae-Hun Kim

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
174 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereocontrolled synthesis of the C 1 C 9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral b-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an a,b-unsaturated d-lactone.

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