Stereoselective synthesis of polyoxygenated atisane-type diterpenoids
Stereoselective synthesis of polyoxygenated atisane-type diterpenoids
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DOI：
10.1016/s0040-4039(01)01953-0
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发表时间：
2001-12-17
影响因子：
1.8
通讯作者：
Navarro, I
中科院分区：
文献类型：
--
作者：
Abad, A;Agulló, C;Navarro, I
描述了一种以 (S)-(+)-香芹酮为原料的多氧化阿蒂烷型二萜的新立体选择性方法。关键步骤涉及分子内第尔斯-阿尔德反应。不饱和酮的不寻常的分子内重氮酮环丙烷化和环丙基羰基的区域选择性环内裂解作为关键的合成步骤。介绍了按照这种方法合成生物活性多氧 atisanes atis-16(17)-en-3,14-dione (2) 和 3R-羟基-atis-16(17)-en-2.14-dione (3)。 (C) 2001 Elsevier Science Ltd. 保留所有权利。
A new stereoselective approach to polyoxygenated atisane-type diterpenes starting from (S)-(+)-carvone is described. The key steps involve an intramolecular Diels-Alder reaction. an unusual intramolecular diazo ketone cyclopropanation of an unsaturated ketone, and a regioselective endocyclic cleavage of a cyclopropyl carbinyl radical as key synthetic steps. The synthesis of the bioactive polyoxygenated atisanes atis-16(17)-en-3,14-dione (2) and 3R-hydroxy-atis-16(17)-en-2.14-dione (3) following this approach is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.