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Total Synthesis of Maoecrystal V
Author(s) -
Zhang WeiBin,
Lin Guang,
Shao WenBin,
Gong JianXian,
Yang Zhen
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403228
Subject(s) - hela , intramolecular force , stereochemistry , total synthesis , terpenoid , chemistry , tetrahydrofuran , organic chemistry , in vitro , biochemistry , solvent
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.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC 50 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 Rh II ‐catalyzed OH insertion reaction.