Synthetic attempts toward alpha-tocopherol-An overview

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作   者：

Kundu, Subhradip;  Sarkar, Debayan; 

作者机构：

Natl Inst Technol; 

关键词：

ACID CATALYST;  8R)-ALPHA-TOCOPHEROL VITAMIN-E;  SIDE-CHAIN;  (2R;  ASYMMETRIC EPOXIDATION;  PLASTOQUINONE SYNTHESIS;  CHEMISTRY;  WHEAT-GERM OIL;  DELTA-TOCOPHEROL;  DIETARY REQUIREMENTS;  4R;  CHROMAN RING; 

期刊名称：

Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry

i s s n：

0022-152X

年卷期：

2023 年 60 卷 3 期

页   码：

345-368

页   码：

摘   要：

The discovery of vitamin E as an essential factor in the diet was a scientific revolution that enlightened the entire world. Vitamin E was discovered in the year 1922 by Herbert M. Evans and K. Scott Bishop and the first synthetic attempt toward alpha-tocopherol appeared almost two decades later through a condensation reaction. During the second world war, similar Lewis acid-catalyzed condensation approaches were accomplished starring 1,3,5-trimethyl hydroquinone and varying the other component. The stereochemistry of the three chiral centers present in the alpha-tocopherol molecule was revealed in the early 1960s and thereafter scientific community took interest in synthesizing natural (2R,4 ' R,8 ' R)-alpha-tocopherol molecule with high enantioselectivity. During the first decade of the 21st century, several groups have applied Bronsted and Lewis acid catalysts to mobilize the condensation reactions toward alpha-tocopherol. In the year 2012, we celebrated 100 years of vitamins and now we are celebrating the 100th anniversary of vitamin E discovery. This historical review highlights key research achievements since the last century and untold stories on alpha-tocopherol and/or vitamin E.