Formal Synthesis of (–)-Siccanin Using an Enantioselective Domino Wacker/Carbonylation/Methoxylation Reaction

Dedicated to Professor Steven V. Ley on the occasion of his 70th birthday

Abstract

A formal synthesis of (–)-siccanin was achieved through an enantioselective domino Wacker/carbonylation/methoxylation reaction as the key step to form the chroman ring with a quaternary stereogenic center with 95% ee. The pendant cyclohexyl moiety was introduced through a two-step aldol condensation.

Key words

natural products - domino reaction - aldol reaction - transition-metal catalysis - enantioselective reactions

• References and Notes

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