A MICROBIAL LIPASE BASED STEREOSELECTIVE SYNTHESIS OF (D)-ALPHA-TOCOPHEROL FROM (R)-CITRONELLAL AND (S)-(6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-YL)ACETIC ACID

被引：0
|
作者：
COFFEN, DL
COHEN, N
PICO, AM
SCHMID, R
SEBASTIAN, MJ
WONG, F
机构：
来源：
HETEROCYCLES | 1994年 / 39卷 / 02期
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D O I：
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of natural vitamin E (2R,4'R,8'R)-alpha-tocopherol) based on (R)-citronellal and (S)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid is described. The citronellal is elaborated into an optically pure C-13 allylic carbonate using a lipase catalyzed kinetic resolution to control the new chiral center. Palladium catalyzed coupling of this C-13 carbonate with either a beta-ketoester or beta-ketosulphone derived from the chromanylacetic acid completes the assembly of the alpha-tocopherol skeleton. Appropriate functional group modifications are used to complete the synthesis.
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页码：527 / 552
页数：26
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