A concise synthesis of the functionalized [5-7-6] tricyclic skeleton of guanacastepene A
A concise synthesis of the functionalized [5-7-6] tricyclic skeleton of guanacastepene A
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DOI：
10.1016/j.tetlet.2004.09.187
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发表时间：
2004-11-22
影响因子：
1.8
通讯作者：
Kwon, OY
中科院分区：
文献类型：
--
作者：
Du, XH;Chu, HFV;Kwon, OY
通过1，1，4-三取代二烯的Diels-Alder反应，在C8四元中心和远端C5立体中心建立了正确的相对立体化学。在Diels-Alder加合物9的10个有效步骤中，合成了所需的高度官能化的[5-7-6]三环骨架2。关键步骤包括三甲基硅氯(TMSCl)协助Michael加成生成烯醇醚，以及在随后的分子内Mukaiyama Aldol反应中使用该烯醇醚形成鸟粪酸A(C)2004 Elsevier Ltd.的中间七元环。保留所有权利。
The six membered ring of guanacastepene A was constructed by a Diels-Alder reaction of 1,1,4-trisubstituted diene to set up the correct relative stereochernistry at the C8 quaternary center and the remote C5 stereocenter. In 10 efficient steps from the Diels-Alder adduct 9, the desired highly functionalized [5-7-6] tricyclic skeleton 2 was synthesized. Key steps involve trimethylsilyl chloride (TMSCl) assisted Michael addition to form enol ether and the usage of the enol ether in the following intramolecular Mukaiyama aldol reaction to form the middle seven membered ring of guanacastepene A. (C) 2004 Elsevier Ltd. All rights reserved.