Total Synthesis of Laingolide B Stereoisomers and Assignment of Absolute Configuration

Organic Letters
Chengsen Cui, Wei-Min Dai

Abstract

Total synthesis of (-)-(2 R,9 S)- and (+)-(2 S,9 S)-stereoisomers of laingolide B has been accomplished by using sequential ring-closing metathesis (RCM) and alkene isomerization to construct the macrocyclic trans- N-methyl enamide moiety. The Myers alkylation was used to secure the C2 stereochemistry of the two RCM precursors from a common (9 S)-C3-C9 alkyl iodide. The absolute configuration of laingolide B has been assigned as (2 S,9 R) by comparison of the optical rotation data.

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep

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