A short multigram asymmetric synthesis of prostanoid scaffolds
A short multigram asymmetric synthesis of prostanoid scaffolds
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DOI：
10.1016/s0040-4020(03)00920-7
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发表时间：
2003-08-25
期刊：
影响因子：
2.1
通讯作者：
Ghosez, L
中科院分区：
文献类型：
--
作者：
Depré, D;Chen, LY;Ghosez, L
Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.
