Ring Expansion from 16‐Membered Macrocyclic Lactones Using Yamaguchi and Photoinduced Decarboxylative Radical Macrolactonization

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI:10.1002/ajoc.202400560
Ryoga Hashimoto , Kenta Kameda , Shoki Kuresawa , Tomoya Iwasaki , Prof. Toshiki Furutani , Prof. Mugen Yamawaki , Prof. Hirotsugu Suzuki , Prof. Yasuharu Yoshimi
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Abstract

This study describes a new strategy for synthesizing 31‐, 33‐, 46‐, and 48‐membered macrocyclic lactones from commercially available 16‐membered macrocyclic lactones using the Yamaguchi reaction and photoinduced decarboxylative radical macrolactonization. Despite challenges with the low solubility of substrates and the slow rate of photochemical radical cyclization, the preparation of enlarged macrocyclic lactones from 16‐membered macrocyclic lactones was successfully accomplished. Additionally, the effect of the Lewis acidity of the counter cation in the carboxylate salt provided mechanistic insights into the photoinduced decarboxylative radical macrolactonization.

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CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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