Total synthesis of amphidinol 3

Yuma Wakamiya, Tohru Oishi

Research output: Contribution to journalArticlepeer-review

Abstract

Amphidinol 3(AM3), a secondary metabolite isolated from the dinoflagellate Amphidinium krebsi, elicits potent antifungal and hemolytic activities. Although the absolute configuration of AM3 was determined by instrumental analysis in combination with degradation of the natural product and chemical correlation in 1999, it was a daunting task, because of the presence of a number of stereogenic centers are located on the acyclic chain and limited availability from natural sources. During the course of our synthetic studies to confirm the structure, the absolute configuration of AM3 was revised. Based on the structure revised in 2018, the first total synthesis of AM3 has been achieved via assemblage of the C1-C29 and the C30-C52 sections by Suzuki-Miyaura coupling, followed by Julia-Kocienski olefination with the C53-C67 section. The spectral data for the synthetic specimen were in agreement with those for the natural product including the sign and magnitude of the specific rotation and antifungal activity, revealing its true structure after more than twenty years since its first discovery. This article describes all the process to prepare the segments and to assemble the segments in the total synthesis of AM3.

Original languageEnglish
Pages (from-to)664-672
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume79
Issue number7
DOIs
Publication statusPublished - Jul 1 2021

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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