Total Synthesis of Aculeatins A and B, and Formal Synthesis of Aculeatin D and 6-epi-Aculeatin D through an Asymmetric Aldol Reaction

Abstract

A versatile and straightforward approach to the total synthesis of the dispirocyclic natural products aculeatins A, B, and D and 6-epi-aculeatin D was developed. The key steps involve a catalytic asymmetric aldol reaction using a titanium(IV) tetraisopropoxide/(S)-[1,1′-binaphthalene]-2,2′-diol system to form a C-2 hydroxy group, a hydroxy-directed­ reduction, and a Weinreb ketone synthesis.

Key words

spiro compounds - medicinal chemistry - total synthesis - asymmetric synthesis - aldol reactions

• Reference

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