Asymmetric syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid as potential antibacterial agents

The first total syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid have been accomplished. Central to this strategy are asymmetric alkynylation of aldehyde, acid‐catalyzed lactonization, the selective protection of primary alcohol and Wittig reaction. The product 1a was obtaine...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2021-11, Vol.33 (11), p.797-809
Main Authors: Wang, Lifeng, Zhou, Yun, Wang, Xueyang, Yuan, Gucheng, Yuan, Chaonan, Yang, Yuxiong, Bian, Qinghua, Wang, Min, Zhong, Jiangchun
Format: Article
Language:English
Subjects:
13‐hydroxy‐14‐methylhexadecanoic acid
Alcohols
Aldehydes
Anti-Bacterial Agents - pharmacology
antibacterial agent
Antibacterial agents
Antiinfectives and antibacterials
asymmetric synthesis
Asymmetry
enantioselective alkynylation
Fatty acids
Hydroxy Acids
lactonization
Palmitic Acids
Stereoisomerism
Stereoisomers
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Summary:The first total syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid have been accomplished. Central to this strategy are asymmetric alkynylation of aldehyde, acid‐catalyzed lactonization, the selective protection of primary alcohol and Wittig reaction. The product 1a was obtained in 17 steps in 2% overall yield. Moreover, these synthetic chiral hydroxy fatty acids 1a‐1d are valuable for the development of antibacterial agents. The total syntheses of four stereoisomers of 13‐hydroxy‐14‐methylhexadecanoic acid (1a‐1d) have been accomplished. The key steps included asymmetric alkynylation of aldehyde, acid‐catalyzed lactonization, the selective protection of primary alcohol and Wittig coupling.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23352