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Synthesis 2023; 55(02): 341-346
DOI: 10.1055/a-1700-3520
DOI: 10.1055/a-1700-3520
paper
Special Issue dedicated to Prof. Alain Krief
Stereoselective Total Synthesis of (+)-Brevipolide H from d-Galactal
This 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).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1700-3520.
- Supporting Information
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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