Synthesis of (2S, 3R)-2-allyl-3-furyl cyclopentanone.: An enantioselective strategy towards the synthesis of phorbol

被引:7
|
作者
Chairgulprasert, V [1 ]
Drew, MGB [1 ]
Jahans, A [1 ]
Harwood, LM [1 ]
机构
[1] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
关键词
chiral; cyclopentenone; phorbol;
D O I
10.3998/ark.5550190.0003.905
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(1S, 5R)-5-(2-furyl)-2-oxocyclopentanecarboxylate 10 was synthesised by asymmetric conjugate addition of lithium difurylcyanocuprate to the chiral substrate 9 in high diastereoisomeric excess (>95 %). After transesterification, allylation and subsequent decarbomethoxylation, (2S, 3R)-2-allyl-3-furyl cyclopentanone 13 was obtained in >86 % ee.
引用
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页码:37 / 45
页数:9
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