Asymmetric total synthesis of (+)-(2R,4′R,8′R)-α-tocopherol enabled by enzymatic desymmetrization-Reference-Cited by-同舟云学术

Asymmetric total synthesis of (+)-(2R,4′R,8′R)-α-tocopherol enabled by enzymatic desymmetrization

Published:2022 Issue:14 Volume:20 Page:2909-2921
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Yang Haidi¹,Liu Jinyao¹,Hu Pan²,Gao Liang²,Huang Zedu¹^ORCID,Chen Fener¹²^ORCID

Affiliation:

1. Department of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, P. R. China

2. Key Laboratory of Green Chemical Engineering Process of Ministry of Education, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, 430205, P. R. China

Abstract

Lipase-catalyzed desymmetric hydrolysis enabled an efficient, stereoselective synthesis of chiral diol (S)-14, the key intermediate to (+)-(2R,4′R,8′R)-α-tocopherol (1).

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Science and Technology Commission of Shanghai Municipality

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D2OB00384H

Reference42 articles.

1. One Hundred Years of Vitamins-A Success Story of the Natural Sciences

2. A year away to 100th year of vitamin E synthesis

3. Stereocontrolled Generation of the (2R) Chroman Core of Vitamin E: Total Synthesis of (2R,4′RS,8′RS)-α-Tocopherol

4. A novel total synthesis of (2R,4'R,8'R)-.alpha.-tocopherol (vitamin E). Construction of chiral chromans from an optically active, nonaromatic precursor

5. Totalsynthese von nat�rlichem ?-Tocopherol. 4. Mitteilung. Aufbau des Chromanringsystems aus Trimethylhydrochinon und einem optisch aktiven C4- bzw. C5-Synthon

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