Synthesis 2023; 55(02): 341-346
DOI: 10.1055/a-1700-3520
paper
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Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal

Ziyang Zhao
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Qingwei Lv
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Jialin Geng
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yang Liu
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Chao Hu
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
,
Yuguo Du
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Jun Liu  ∗
a   State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Science, Beijing 100085, P. R. of China
b   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
› Author AffiliationsThis work was supported by the STS Project of Chinese Academy of Sciences (KFJ-STS-QYZD-201-5-1) and the National Key Research and Development Program of China (2019YFC1605802).
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Abstract

An efficient and concise synthesis of cytotoxic 5,6-dihydro-α-pyrone (+)-brevipolide H has been accomplished in 12 long linear steps in 8.65% overall yield from readily available chiral synthons, d-galactal and ethyl l-lactate. The features of this synthesis are highly diastereoselective Simmons–Smith cyclopropanation and carbohydrate-based chiron approach to rapid access to key 5,6-dihydro-α-pyrone skeleton.

Key words

(+)-brevipolide H - total synthesis - 5,6-dihydro-α-pyrone - d-galactal - chiron approach

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1700-3520.
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Publication History

Received: 26 October 2021

Accepted after revision: 17 November 2021

Accepted Manuscript online:
17 November 2021

Article published online:
12 January 2022

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