Stereoselective synthesis of (R)-(-) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone
Stereoselective synthesis of (R)-(-) and (S)-(+)-phoracantholide I from (R)-(+)-γ-valerolactone
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DOI：
10.1016/j.tetasy.2016.05.008
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发表时间：
2016-08-15
影响因子：
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通讯作者：
Pratap, T. V.
中科院分区：
文献类型：
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作者：
Datrika, Rajender;Kallam, Srinivasa Reddy;Pratap, T. V.
以（R）-（+）-γ-戊内酯6为起始原料，经全合成得到（R）-（-）-佛刺丁素I 1和（S）-（+）-佛刺丁素I 2。合成这些大环内酯的关键步骤包括乙酰丙酸酯4通过不对称脱氢酶的酶促还原，（4-羧基丁基）三苯基膦叶立德11与内半缩醛7的Z-选择性Wittig反应，以及开环酸8使用Yamaguchi内酯化方案或Mitsunobu方案分别环化以得到（R）-（-）-phoracanthropine I和（S）-（+）-phoracanthropine I。(C)2016爱思唯尔有限公司版权所有。
A concise total synthesis of (R)-(-)-phoracantholide I 1 and (S)-(+)-phoracantholide I 2 has been developed from (R)-(+)-gamma-valerolactone 6. The key steps in the synthesis of these macrolides involved enzymatic reduction of Levulinic ester 4 by asymmetric dehydrogenase, Z-selective Wittig reaction of (4-carboxybutyl)triphenylphosphonium ylide 11 with lactol 7, and cyclization of seco-acid 8 using either a Yamaguchi lactonization protocol or a Mitsunobu protocol to afford (R)-(-)-phoracantholide I and (S)-(+)-phoracantholide I respectively. (C) 2016 Elsevier Ltd. All rights reserved.