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
a   Yunnan 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
a   Yunnan 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
a   Yunnan 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
a   Yunnan 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
a   Yunnan 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
b   School of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China
,
Wen-Jing Wang
a   Yunnan 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∗
b   School of Chemistry and Chemical Engineering, Yunnan Normal University, 798 Jvxian Street, Kunming, 650500, P. R. of China
,
Li-Dong Shao  ∗
a   Yunnan 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
› Author AffiliationsThe authors gratefully acknowledge financial support from the National­ Natural Science of Foundation of China (81960631), the Yunnan­ Fundamental Research Project (202001AS070038), the Ten Thousand Talent Plans for Young Top-Notch Talents of Yunnan Province (R.Z. and L.-D.S.), and the Start-up Fund of Yunnan University of Chinese Medicine (2019YZG03).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1878-8597.
  • Supporting Information


Publication History

Received: 27 May 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
11 August 2022

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