Asymmetric Total Synthesis of (+)-Acaulone B.

Authors

Sho Fujii, Jun Hirabayashi, Akira Katsuyama, Satoshi Ichikawa, Fumika Yakushiji

Published in

The Journal of organic chemistry. Jun 23, 2026. Epub Jun 23, 2026.

Abstract

Acaulone B (1) was isolated from Acaulium sp. H-JQSF. The cyclohexenone moiety of 1 was constructed via late-stage chemo-, regio-, and stereoselective Diels-Alder reactions between a diene unit and the C8-C9 double bond of the 14-membered macrodiolide. The regioselectivity of the [4 + 2] cycloaddition was analyzed by DFT calculations, which showed the lowest Gibbs energy of the TS structure and asynchronous cycloaddition. Our investigation demonstrates the effectiveness of late-stage functionalization of macrocycles to synthesize complex natural products.

PMID:
42335375
Bibliographic data and abstract were imported from PubMed on 24 Jun 2026.

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