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Total Synthesis of (-)-Enigmazole B.

Yoshihiro GodaHaruhiko Fuwa
Published in: Organic letters (2023)
Total synthesis of (-)-enigmazole B was achieved for the first time. Highlights of the present synthesis include an olefin cross-metathesis and hemiacetalization/intramolecular oxa-Michael addition sequence for accessing an ( E )-configured enol tosylate, a Sonogashira cross-coupling to assemble all the carbon atoms of the target natural product, a remarkably chemo- and regioselective Au-catalyzed intramolecular alkyne hydroalkoxylation for the construction of the dihydropyran ring, and a Yamaguchi macrolactonization to close the 18-membered macrolactone skeleton.
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