CAROTENOIDS WITH 7-OXABICYCLO[2.2.1]HEPTYL END GROUPS .2. SYNTHESIS OF (2S,5R,6S,2'S,5'R,6'S)-2,5-2',5'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE

被引:3
作者
GMUNDER, MR [1 ]
EUGSTER, CH [1 ]
机构
[1] UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
关键词
D O I
10.1002/hlca.19900730816
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carotenoids mit 7‐Oxabicyclo[2.2.1]heptyl‐End Groups. Synthesis of (2S,5R,6S,2′S,5′R,6′S)‐2,5:2′5′‐Diepoxy‐5,6,5′,6′‐tetrahydro‐β,β‐carotene Mukayama's ester 6 (methyl (1S,2R,5S)‐2,5‐epoxy‐2,6,6‐trimethylcyclohexane‐1‐carboxylate) was transformed in a few conventional steps into the title compound 14. Its CD curve was found to be significantly different from that of the analogous 3,6‐epoxide, a fact we tentatively lake as an indication of a (weak) electronic interaction between the ring O‐atom and the π‐orbitals of the polyene chain. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim
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页码:2190 / 2198
页数:9
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