Embracing the Imperfectness of Nature using Highly Reactive N-Acyl Azahexatrienes

Kuan Zheng; Bingbing Zhang; Ran Hong

doi:10.1055/a-2066-1227

Synlett, Table of Contents

Synlett 2024; 35(05): 513-520
DOI: 10.1055/a-2066-1227

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Biomimetic Synthesis

Embracing the Imperfectness of Nature using Highly Reactive N-Acyl Azahexatrienes

Authors

Kuan Zheng∗

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Bingbing Zhang

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 101419, P. R. of China
Ran Hong∗

^aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 101419, P. R. of China

Abstract

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Abstract

Incredible examples of controlling highly reactive functional groups to synthesize amazing architectures can be found in nature. N-Acyl azahexatriene, which is involved in biosynthesis, is clearly among them, despite the extremely limited number of examples disclosed in the literature. We explored the biomimetic synthesis of macrocarbocyclic natural products, chejuenolides A–C, as well as structural variants, to unveil the hidden stereochemical relationships between their biosynthesis and those of lankacidin antibiotics. This revealed the logic of the reaction pattern, which was likely influenced by catalytic promiscuity in nature.

Key words

antibiotic - biomimetic synthesis - chejuenolide - macrocyclization - Mannich

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