Synthesis of γ‑Lactones via the Kowalski Homologation Reaction: Protecting-Group-Free Divergent Total Syntheses of Eupomatilones-2,5,6, and 3-epi-Eupomatilone‑6

A highly efficient synthesis of functionalized chiral γ-butyrolactone scaffolds has been described. The basis of the approach is the Kowalski ester homologation that is modified for our proposed transformation. The newly developed methodology combines a divergent synthetic strategy to permit a strai...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (19), p.7857-7862
Main Authors: Choi, Hosam, Jang, Hanho, Kim, Hyoungsu, Lee, Kiyoun
Format: Article
Language:English
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Summary:A highly efficient synthesis of functionalized chiral γ-butyrolactone scaffolds has been described. The basis of the approach is the Kowalski ester homologation that is modified for our proposed transformation. The newly developed methodology combines a divergent synthetic strategy to permit a straightforward protecting-group-free asymmetric total syntheses of eupomatilones-2,5,6, and 3-epi-eupomatilone-6 in five or six steps from commercial starting materials, making it one of the shortest syntheses reported to date.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02848