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Total Synthesis of Caldorazole, a Potent Mitochondrial Respiratory Chain Inhibitor without Chiral Centers

2023; American Chemical Society; Volume: 88; Issue: 5 Linguagem: Inglês

10.1021/acs.joc.2c03007

1520-6904

Yuta Miyamoto, Arihiro Iwasaki, Haruka Fujimura, Chihiro Kudo, Naoaki Kurisawa, Osamu Ohno, Kiyotake Suenaga,

Chemical Synthesis and Analysis

Caldorazole (1) is a novel polyketide that was isolated from a marine cyanobacterium in 2022. It is a unique natural product that exhibits potent inhibitory activity against mitochondrial respiratory chain complex I despite having no chiral centers. To establish a method for obtaining caldorazole without relying on biological resources and for constructing a useful synthetic route for studies of its structure–activity relationship, we achieved the first total synthesis of caldorazole using a convergent synthetic route.