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- Title
Total Synthesis of Maoecrystal V.
- Authors
Zhang, Wei ‐ Bin; Lin, Guang; Shao, Wen ‐ Bin; Gong, Jian ‐ Xian; Yang, Zhen
- Abstract
Maoecrystal V ( 1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun et al. It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20 ng mL−1. Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (±)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels-Alder reaction, and a RhII-catalyzed OH insertion reaction.
- Subjects
DITERPENES synthesis; HERBAL medicine; HELA cells; TETRAHYDROFURAN synthesis; DIELS-Alder reaction; DEAMINATION
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 4, p903
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201403228