Highly Diastereoselective Synthesis of 2,2-Disubstituted Cyclopentane-1,3-diols via Stepwise Ketone Reduction Enabling Concise Chirality Construction

被引：4

作者：

Gong, Jingyao ^{[1
,3
]}

Li, Jianjiong ^{[1
,2
]}

Chen, Xi ^{[1
,2
]}

Zhang, Hongliu ^{[1
,2
]}

Zhu, Liangyan ^{[1
,2
]}

Bu, Dandan ^{[1
,2
]}

Wang, Qin ^{[3
]}

Feng, Jinhui ^{[1
,2
]}

Wu, Qiaqing ^{[1
,2
]}

Zhu, Dunming ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Natl Engn Lab Ind Enzymes, Tianjin 300308, Peoples R China

[2] Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin Engn Res Ctr Biocatalyt Technol, Tianjin 300308, Peoples R China

[3] Southwest Med Univ, Dept Med Chem, Sch Pharm, Luzhou 646000, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 15期

基金：

国家重点研发计划; 中国国家自然科学基金;

关键词：

ASYMMETRIC MICROBIAL REDUCTION; CONVERGENT TOTAL-SYNTHESIS; HYDROXY KETONES; DESYMMETRIZATION;

D O I：

10.1021/acs.joc.0c00851

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2,2-disubstituted trans,cis-cyclopentane-1,3-diols were synthesized in >99% dr through enzymatic reduction of enantiopure 2,2-disubstituted 3-hydroxycyclopentane-1-ones, which were prepared by highly stereoselective enzymatic reduction of the corresponding cyclo-diketones. For 2-benzyl-2-methyl-3-oxocyclopentyl acetate, acetylation of the hydroxyl group significantly affected the reduction stereoselectivity, giving trans,cis-, trans,trans-, and cis,cis-2-benzyl-2-methyl-cyclopentane-1,3-diols in stereomerically pure form. This efficient and environmentally friendly method provides a practical approach to the synthesis of these chiral building blocks in single stereoisomeric form, demonstrating the power of biocatalysis in the concise chirality construction of complex chiral molecules.

引用

页码：9599 / 9606

页数：8

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