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
关键词：
D O I：
暂无
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.
引用
收藏
页码：527 / 552
页数：26
相关论文
共 22 条
  • [21] Absolute structure of (3aS,5S,7aS,7bS,9aR,10-S,5S,7aS,7bS,9aR,10R,12aR,12bS)-7b-hydroxy4,4,7a,9a,12a-pentamethyl-10-[(2′R)-6-methylheptan-2-yl]-2,8,9-trioxooctadecahydrobenzo[d]indeno[4,5-b] azepin-5-yl acetate from 62-year-old crystals
    Suescun, Leopoldo
    Heinzen, Horacio
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 1348 - +
  • [22] Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
    Li, Shi-Qing
    Zhou, Jian
    Dong, Zhang-Chao
    Pan, Bo Wen
    Shi, Yang
    Zhou, Ying
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2023, 238 (04): : 735 - 737
123