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Synlett 2021; 32(14): 1469-1472
DOI: 10.1055/s-0040-1720348
DOI: 10.1055/s-0040-1720348
letter
Efficient Construction of (±)-epi-Costunolide through a Chromium(II)-Mediated Nozaki–Hiyama–Kishi Reaction
Authors
This work was supported by the National Natural Science Foundation of China (grants: 21877062, YZ; 81803342, LH), the key research projects of Jiangsu Higher Education (No. 18KJA360010, YZ), and the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant: 18KJD360001).
Abstract
(±)-epi-Costunolide has been synthesized through a seven-step procedure starting from (E,E)-farnesol. The key step includes an intramolecular allylation of an aldehyde through a chromium(II)-mediated Nozaki–Hiyama–Kishi reaction, in which more than one equivalent of CrCl2 has been recognized as the most effective reagent to promote the conversion. An anti-inflammatory screen showed that epi-costunolide is a moderate inhibitor of B lymphocyte proliferation.
Key words
costunolide - germacrenes - Nozaki–Hiyama–Kishi reaction - total synthesis - medicinal chemistry - sesquiterpenoid lactonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720348.
- Supporting Information (PDF) (opens in new window)
Publication History
Received: 07 June 2021
Accepted after revision: 25 June 2021
Article published online:
13 July 2021
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