Synthesis of the Trans-Syn-Trans Perhydrobenzo[f]chromene Ring System

04 May 2021, Version 1

Abstract

A stereoselective synthesis of the trans-syn-trans perhydrobenzo[f]chromene skeleton is presented. The target compound 3 was achieved in six steps starting from the (S)-(+)-Wieland-Miescher ketone. Key steps include the sp2 alkylation at the a-carbon of an unsaturated ketone, Birch-type reductive alkylation, and an acid-catalyzed cyclization.

Keywords

meroterpenoids
regioselective alkylations
Stereochemistry
fungal natural products

Supplementary materials

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