bufogargarizin B的简洁形式化合成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-28 DOI:10.1016/j.tetlet.2025.155627

Yuxin Xie, Huiling Yang, Yuxuan Tang, Jie Zhao, Hailian Li, Liang Xu

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引用次数: 0

摘要

以市售雌酮8为原料，以36%的总收率，用8步合成了先进的[5-7-6-5]四环中间体II，实现了一种简洁、可扩展的正态合成丁fogargarizin B。该合成的主要特点是羰基的立体选择性还原和氧化裂解/跨环醛醇级联反应，以快速构建重排的A/B环体系和三个立体中心。本研究提出了一种新的合成方法，以获得bufogargarizin B和相关类固醇的独特重排框架。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A concise formal synthesis of bufogargarizin B

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A concise formal synthesis of bufogargarizin B

A concise and scalable formal synthesis of bufogargarizin B has been achieved by completing the synthesis of the advanced [5–7–6–5] tetracyclic intermediate II in 8 steps with 36 % overall yield from commercially available estrone 8. Key features of the synthesis include stereoselective reduction of the carbonyl group and an oxidative cleavage/transannular aldol cascade reaction to rapidly construct the rearranged A/B ring system and three stereogenic centers. This study presents a new synthetic approach to the unique rearranged framework of bufogargarizin B and related steroids.

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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.