Concise organocatalyzed epoxidation based total synthesis of (−)- and (+)-trans-posticlures and (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene†

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-04-24 DOI:10.1039/D5OB00597C

Rodney A. Fernandes and Gulenur N. Khatun

引用次数: 0

Abstract

A concise, flexible and efficient organocatalytic strategy has been developed for the enantioselective synthesis of (−)-trans- and (+)-trans-posticlures, along with (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene which are remarkable natural trans-epoxide pheromones. The key transformations in this approach involve an organocatalyzed asymmetric Jørgensen epoxidation and stereoselective (Z)-Wittig olefination. Notably, the Jørgensen epoxidation step ensures excellent enantiopurity (up to 97% ee) in the synthesis of the target pheromone antipodes.

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基于简洁有机催化环氧化的(-)-和(+)-反式位姿和(-)-(6Z,9Z,4S,5S)-反式4,5-环氧壬二烯的全合成

摘要为对映选择性合成(-)-反式和(+)-反式后位化合物以及(-)-(6Z,9Z,4S,5S)-反式4,5-环氧壬二烯这两种重要的天然反式环氧信息素，开发了一种简洁、灵活、高效的有机催化策略。该方法的关键转化包括有机催化的不对称Jørgensen环氧化和立体选择性(Z)-Wittig烯烃。值得注意的是，Jørgensen环氧化步骤确保了目标信息素对映体的合成具有优异的对映纯度（高达97% ee）。

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

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.