Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-D-mannitol
Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-D-mannitol
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DOI：
10.1016/j.tet.2005.04.059
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发表时间：
2005-07-04
期刊：
影响因子：
2.1
通讯作者：
Nakata, T
中科院分区：
文献类型：
--
作者：
Takahashi, S;Ogawa, N;Nakata, T
描述了一种从2，5-脱水-D-甘露醇（1）制备天然β-羟基-γ-内酯2的新方法。该合成中的关键反应包括醛3与二甲基铜酸锂的立体选择性甲基化、硒代碳酸酯11的分子内自由基环化和3-烯丙基-4-羟基-γ-内酯16与1-十三烯的分子间交叉易位。(c)2005爱思唯尔有限公司保留所有权利。
A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.