Concise synthesis of (±)-gomadalactone A

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-29 DOI:10.1016/j.tetlet.2025.155623

Ryosuke Ashizaki, Ryo Katsuta, Shinnosuke Wakamori, Tomoo Nukada, Ken Ishigami

引用次数: 0

Abstract

We report the synthesis of (±)-gomadalactone A, a contact sex pheromone of the white-spotted longicorn beetle (Anoplophora malasiaca). The synthesis employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis from a furan derivative, followed by lactonization, to efficiently construct a distinctive 3-oxabicyclo[3.3.0]octane framework. This eleven-step process starts from methyl 2-furylacetate, produced (±)-gomadalactone A in an overall yield of 1 %.

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（±）-戈马达拉内酯A的简明合成

报道了白斑天牛（Anoplophora malasiaca）接触性信息素（±）-gomadalactone A的合成。该合成采用Vassilikogiannakis的一锅光驱动环戊酮合成法，由呋喃衍生物合成，然后内酯化，有效地构建了独特的3-恶比环[3.3.0]辛烷值框架。这个11步工艺从2-呋喃乙酸甲酯开始，以1%的总收率生产（±）-戈马达拉内酯A。

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

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.