Asymmetric Total Synthesis of (+)-Ineleganolide.

Authors

Changhong Han, Yichi Zhang, Yuxin Tian, Ziang Ding, Zhou Pan, Junhong Li, Weiwu Ren

Published in

Angewandte Chemie (International ed. in English). Pages e2110292. Jul 13, 2026. Epub Jul 13, 2026.

Abstract

Polycyclic cembrane diterpenoids and norditerpenoids have garnered sustained interest from the synthetic community due to their unique polycyclic frameworks and promising biological activities. Herein, we report a 13-step total synthesis of (+)-ineleganolide, a highly oxidized cembrane norditerpenoid possessing a synthetically challenging [6,7,5,5,5] cage-type pentacyclic scaffold. This synthesis is highlighted by a novel strategy relying on an intramolecular Diels-Alder reaction that stereoselectively constructs the pivotal [6,6,5,5,5] pentacyclic framework as a single diastereoisomer, addressing stereochemical control challenges. In the late-stage elaboration, a tandem epoxidation/Meinwald rearrangement efficiently forges the sterically congested central seven-membered ring. This synthetic strategy provides a new blueprint for accessing other members of the cembrane norditerpenoid family.

PMID:
42438972
Bibliographic data and abstract were imported from PubMed on 13 Jul 2026.

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