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

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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)3208-3216
Number of pages9
JournalJournal of Organic Chemistry
Volume88
Issue number5
DOIs
Publication statusPublished - 2023 Mar 3

ASJC Scopus subject areas

  • Organic Chemistry

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