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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Published in:Organic letters 2019-10, Vol.21 (19), p.7857-7862
Main Authors: Choi, Hosam, Jang, Hanho, Kim, Hyoungsu, Lee, Kiyoun
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Language:English
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cited_by cdi_FETCH-LOGICAL-a345t-e145fed09b97acd899b6ae7615a14ff282e6139feba5d0667e73f5700e8dea363
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container_title Organic letters
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creator Choi, Hosam
Jang, Hanho
Kim, Hyoungsu
Lee, Kiyoun
description 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.
doi_str_mv 10.1021/acs.orglett.9b02848
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title 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
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