Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Sho Imaoka; Yuta Nakashima; Mariko Kitajima; Hayato Ishikawa

doi:10.1248/cpb.c23-00654

Regular Article

Bioinspired Total Synthesis of (+)-Kopsiyunnanine B

Sho Imaoka ^†, Yuta Nakashima ^†, Mariko Kitajima, Hayato Ishikawa

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Keywords: bioinspired reaction, total synthesis, oxindole alkaloid, cascade reaction, Kopsia alkaloid

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Supplementary material

2024 Volume 72 Issue 1 Pages 68-74

DOI https://doi.org/10.1248/cpb.c23-00654

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Abstract

The first enantioselective total synthesis of kopsiyunnanine B, which has a unique folded and complex pentacyclic structure containing six contiguous chiral centers, has been achieved along our originally proposed biosynthetic pathway. The key reaction of this synthesis includes a bioinspired cascade that builds three ring structures and three chiral centers in one step and features the stereoselective reduction of a β-acrylate and oxidation to an oxindole.

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