A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Yang Chen; Xin-Ting Hu; Xiao-Yan Xie; Dashan Li; Chun-Xia Zheng; You-Xi Zhang; Wen-Jing Wang; Rui Zhan; Li-Dong Shao

doi:10.1055/a-1878-8597

Synthesis, Table of Contents

Synthesis 2023; 55(02): 289-296
DOI: 10.1055/a-1878-8597

paper

Special Issue dedicated to Prof. Alain Krief

A Practical Approach to 6H-Indol-6-ones Enables the Formal Synthesis of γ-Lycorane

Yang Chen

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

Xin-Ting Hu

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

Xiao-Yan Xie

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

Dashan Li

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

Chun-Xia Zheng

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

You-Xi Zhang

^bSchool of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China

,

Wen-Jing Wang

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

,

Rui Zhan∗

^bSchool of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China

,

Li-Dong Shao ∗

^aYunnan Key Laboratory of Southern Medicinal Resources, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, 1076 Yuhua Road, Kunming, 650500, P. R. of China

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Abstract

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Abstract

We represented herein a two-step synthesis of 1-methyl-6H-indol-6-one which is an N-containing 6/5 fused bicyclic building blocks in Amaryllidaceae alkaloids. The key step featured is a ‘one-pot’ ozonolysis/reductive amination/cyclization of allylated cyclohexa-1,3-dione to give bicyclic compounds. Moreover, the formal total synthesis of natural product γ-lycorane could be achieved through a photo-promoted cyclization/oxidation cascade reaction from the resulting bicyclic intermediate.

Key words

1-methyl-6H-indol-6-one - two-step synthesis - one-pot - Amaryllidaceae alkaloids - γ-lycorane

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