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

摘要

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.