Formal total synthesis of neodysiherbaine A via a stereoselective [3+2]-annulation strategy

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-10 DOI:10.1016/j.tet.2025.134934

Koki Hotoda, Shoichi Minato, Ikuo Sasaki, Hideyuki Sugimura

引用次数: 0

Abstract

The highly stereoselective synthesis of the hexahydrofuro[3,2-b]pyran core of neodysiherbaine A is described. The key step involves the stereocontrolled formation of the tetrahydrofuran ring via a formal [3 + 2]-annulation between isopropylidene-protected aldehydo-d-ribose and a β-substituted allylsilane mediated by trifluoroborane etherate.

Abstract Image

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通过立体选择[3+2]环化策略正式全合成新西芹碱A

报道了新酞菁A六氢呋喃[3,2-b]吡喃核的高立体选择性合成。关键步骤是通过异丙基保护的醛核糖和三氟硼醚介导的β取代烯丙基硅烷之间的正式[3 + 2]环形成立体控制的四氢呋喃环。

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 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.