Synlett 2015; 26(14): 2019-2023
DOI: 10.1055/s-0034-1378784
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© Georg Thieme Verlag Stuttgart · New York

A Concise and Versatile Total Synthesis of All Stereoisomers of Tarchonanthuslactone

Shuangping Huang
a   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China   Email: 2012207455@tju.edu.cn
,
Dongwang Liu
a   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China   Email: 2012207455@tju.edu.cn
,
Linjun Tang
b   School of Life Science, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China
,
Feifei Huang
a   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China   Email: 2012207455@tju.edu.cn
,
Wei Yang
c   Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, 518055 Shenzhen, Guangdong, P. R. of China
,
Xiaoji Wang*
a   School of Pharmacy, Jiangxi Science and Technology Normal University, 330013 Nanchang, Jiangxi, P. R. of China   Email: 2012207455@tju.edu.cn
› Author Affiliations
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Publication History

Received: 25 March 2015

Accepted after revision: 10 June 2015

Publication Date:
30 July 2015 (online)


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Abstract

We describe the versatile and concise total synthesis of all stereoisomers of tarchonanthuslactone from (R)- or (S)-3-hydroxybutyrate via eight steps. The key steps of the synthesis include a highly diastereoselective chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde and a Yamaguchi lactonization of a δ-hydroxy-trans-α,β-unsaturated carboxylic acid.

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