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

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

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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