不对称全合成(+)-螺帕那胺G。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-09-05 DOI:10.1021/acs.orglett.5c03226

Yongqi Lin, Freda F. Li* and Margaret A. Brimble*,

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引用次数: 0

摘要

Spiroapplanatumine G(7)是一种特殊的6/5/7三环螺苯并呋喃-3- 1核的螺-巯基萜类化合物。报道了首个对映选择性全合成螺苯二胺G(7)的实验，其中一个关键的对映选择性Diels-Alder反应发生在一个aurone酯和一个硅氧基二烯之间，以组装螺苯并呋喃酮核心。这种战略性的Diels-Alder转换有利于在一个步骤中建立两个连续的立体中心。随后的环丙烷化/ fecl3介导的氧化环扩张提供了所需的三环框架。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric Total Synthesis of (+)-Spiroapplanatumine G

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Asymmetric Total Synthesis of (+)-Spiroapplanatumine G

Spiroapplanatumine G (7) is a spiro-meroterpenoid characterized by an unusual 6/5/7 tricyclic spirobenzofuran-3-one core. The first enantioselective total synthesis of spiroapplanatumine G (7) is reported, featuring a key enantioselective Diels–Alder reaction between an aurone ester and a silyloxydiene to assemble the spirobenzofuranone core. This strategic Diels–Alder transformation advantageously establishes the two contiguous stereogenic centers in a single step. Subsequent cyclopropanation/FeCl₃-mediated oxidative ring expansion affords the desired tricyclic framework.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.