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...

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Published in:Synthesis (Stuttgart) 2015-05, Vol.47 (9), p.1303-1308
Main Authors: Huang, Shuangping, Chen, Shipeng, Wang, Gaopeng, Zhang, Jianting, Tang, Linjun, Du, Guangyan, Wang, Xiaoji
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Language:English
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container_issue 9
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container_title Synthesis (Stuttgart)
container_volume 47
creator Huang, Shuangping
Chen, Shipeng
Wang, Gaopeng
Zhang, Jianting
Tang, Linjun
Du, Guangyan
Wang, Xiaoji
description 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.
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title Total Synthesis of Aculeatins A and B, and Formal Synthesis of Aculeatin D and 6-epi-Aculeatin D through an Asymmetric Aldol Reaction
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