Lewis-acid-promoted reactions of 1-{[(2-methoxyethoxy)methoxy](tributylstannyl)methyl}cyclohexene

被引：0
|
作者：
Muller, B [1 ]
Ferezou, JP [1 ]
Pancrazi, A [1 ]
Lallemand, JY [1 ]
机构：
[1] ECOLE POLYTECH,CNRS,ORGAN SYNTH LAB,DCSO,F-91128 PALAISEAU,FRANCE
来源：
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1997年 / 134卷 / 01期
关键词：
alpha-alkoxyallylic stannane; homoaldol reaction; homoallylic alcohol; Lewis-acid-promoted reaction; synthesis; taxol; taxotere;
D O I：
暂无
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
As a model for a synthetic approach to taxol and taxotere, the condensation of racemic alpha-alkoxy allylic stannane 9 with aldehydes 10a-h was examined. Under BF3 . OEt(2)-promoted reaction conditions, the syn-E 11a-h homoallylic alcohols were obtained as the major isomers. EtAlCl(2) was found to be an efficient promoter for the condensation of aldehyde 10e,f. With beta- or alpha-hydroxyaldehydes 10g or 10h in the presence of intramolecular chelated MgBr2, the stereochemical outcome of the reaction was inverted to give, in high yield and good stereoselectivity, the anti-E 11g,h homoaldol products exhibiting the stereochemistry required for the synthesis of taxanes.
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页码：13 / 25
页数：13
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