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

Authors :
Li-Dong Shao
Rui Zhan
Yang Chen
Xin-Ting Hu
Xiao-Yan Xie
Dashan Li
Chun-Xia Zheng
You-Xi Zhang
Wen-Jing Wang
Source :
Synthesis. 55:289-296
Publication Year :
2022
Publisher :
Georg Thieme Verlag KG, 2022.

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.

Subjects

Subjects :
Organic Chemistry
Catalysis

Details

ISSN :
1437210X and 00397881
Volume :
55
Database :
OpenAIRE
Journal :
Synthesis
Accession number :
edsair.doi...........6b0c66446dd0d664c18d7cbbba5d9aca
Full Text :
https://doi.org/10.1055/a-1878-8597