Total Synthesis of Maoecrystal V
Total Synthesis of Maoecrystal V
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Maoecrystal V的全合成
DOI：
10.1002/asia.201403228
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发表时间：
2015
影响因子：
4.1
通讯作者：
Yang Zhen
中科院分区：
文献类型：
--
作者：
Zhang Wei-Bin;Lin Guang;Shao Wen-Bin;Gong Jian-Xian;Yang Zhen
Maoecrystal V（1）是一种新的二萜类化合物，最初由Sun et al.1从中国草药Isodon eriocalyxin 2004的叶子中分离出来。已发现对HeLa细胞具有选择性细胞毒性，IC 50值为20 ng mL−1。 由于其独特的生物学性质、稀有性和复杂的结构特征，大量的研究工作都致力于其合成。在本文中，我们描述了我们最近的研究，这些研究最终实现了（±）-maoecrystal V的全合成。目前的策略涉及成功构建关键四氢呋喃氧杂桥骨架的三个关键步骤，包括Wessely氧化脱芳构化，新型分子内Diels-Alder反应和RhII催化的O-OH插入反应。
Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herbIsodon eriocalyxin 2004 by Sun et al.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50value 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.