A linear approach for the total synthesis of sex pheromone (3S, 5R, 6S)-6-isopropyl-3,5-dimethyltetrahydro-2H-pyran-2-one and prelactone B

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-01-11 DOI:10.1080/00397911.2025.2449591

Manohar Surve , Naresh Gantasala , Sudheer Pudi , Srihari Pabbaraja

引用次数: 0

Abstract

A linear 10-step approach for the stereoselective total synthesis of (3S,5R,6S)-6-isopropyl-3,5-dimethyltetrahydro-2H-pyran-2-one, the sex pheromone component of Macrocentrus grandii is presented. The key steps involve an enantioselective cross Aldol reaction between isobutyraldehyde and propionaldehyde, a chiral auxiliary mediated diastereoselective methylation reaction, chemoselective reduction of α,β-unsaturated ester and chemoselective oxidation reaction to get lactone. A similar strategy has been applied for the total synthesis of prelactone B.

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全合成性信息素(3S, 5R, 6S)-6-异丙基-3,5-二甲基四氢- 2h -吡喃-2-酮和预内酯B的线性方法

采用线性十步法立体选择性合成了大红花性信息素成分(3S,5R,6S)-6-异丙基-3,5-二甲基四氢- 2h -吡喃-2-酮。其关键步骤包括异丁醛和丙醛之间的对映选择性交叉醛反应、手性助剂介导的非对映选择性甲基化反应、α、β-不饱和酯的化学选择性还原反应和化学选择性氧化反应得到内酯。类似的策略已应用于前内酯B的全合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.