苯二酚3 C22-C29和C20-C29片段的合成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-08 DOI:10.1016/j.tetlet.2025.155586

Yuki Yamashita, Yuma Wakamiya, Yusuke Mita, Yoko Yasuno, Tohru Oishi

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引用次数: 0

摘要

合成了AM3的C22-C29和C20-C29部分对应的多元醇片段，作为AM3人工类似物的构建块，用于构效关系研究。以(S)-Roche酯为原料，在流动和间歇条件下经过连续半还原和Grignard反应，再经过臭氧分解和Grignard反应合成C22-C29。C20-C29段是由AM3的共同中间体和C21-C67段对应的人工类似物经烯烃化和Sharpless不对称二羟基化反应合成的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Syntheses of C22–C29 and C20–C29 sections of amphidinol 3

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Syntheses of C22–C29 and C20–C29 sections of amphidinol 3

Polyol segments corresponding to C22–C29 and C20–C29 sections of amphidinol 3 (AM3) were synthesized as building blocks of artificial analogues of AM3 for structure–activity relationship studies. The C22–C29 section was synthesized from (S)-Roche ester through continuous half-reduction of an ester and a Grignard reaction under flow and batch conditions, followed by iterative ozonolysis and Grignard reactions. The C20–C29 section was derived from the common intermediate of AM3 and the artificial analogue corresponding to the C21–C67 section via olefination and Sharpless asymmetric dihydroxylation.

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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.