Cannabis. Part 25. Synthesis of cannabispirenone-B and its 5,7-difluoro-analogue

Abstract
The naturally occurring cannabispirenone-B (1a) was synthesized by spiroannelation of the piperidine enamine of 5,7-dimethoxyindan-1-carbaldehyde to O-methylcannabispirenone (1b), followed by selective demethylation with lithium iodide in 2,4,6-collidine. Its 5,7-difluoro-analogue (10) was synthesized by spiroannelation of 5,7-difluoroindan-1-carbaldehyde obtained by homologation of 5,7-difluoroindan-1-one, which was synthesized from 1-bromo-3,5-difluorobenzene in three steps.

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