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

Shuangping Huang; Shipeng Chen; Gaopeng Wang; Jianting Zhang; Linjun Tang; Guangyan Du; Xiaoji Wang

doi:10.1055/s-0034-1380228

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1303-1308
DOI: 10.1055/s-0034-1380228

paper

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

Shuangping Huang

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

,

Shipeng Chen

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

,

Gaopeng Wang

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

,

Jianting Zhang

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

,

Linjun Tang

^bSchool of Life Science, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

,

Guangyan Du

^cLaboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, Guangdong, P. R. of China Email: 2012207455@tju.edu.cn

,

Xiaoji Wang*

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, P. R. of China

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Abstract

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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

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References

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