Enantioselective synthesis of (-)-roccellaric acid

被引:93
作者
Böhm, C [1 ]
Reiser, O [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
关键词
D O I
10.1021/ol015686u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new strategy for the synthesis of anti-4,5-disubstituted gamma -butyrolactones starting from inexpensive furan-2-carboxylic methyl ester was developed. By applying this methodology, the enantioselective synthesis of (-)-roccellaric acid ((-)-17) was accomplished using a copper(1)catalyzed asymmetric cyclopropanation, a tin(IV)-catalyzed retroaldol/lactonization sequence of cyclopropanols, and a ruthenium-catalyzed intermolecular metathesis reaction as key steps.
引用
收藏
页码:1315 / 1318
页数:4
相关论文
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[21]  
2-D
[22]   POLYENE SYNTHESIS - READY CONSTRUCTION OF RETINOL CAROTENE FRAGMENTS, (+/-)-6(E)-LTB3 LEUKOTRIENES, AND CORTICROCIN [J].
WENKERT, E ;
GUO, M ;
LAVILLA, R ;
PORTER, B ;
RAMACHANDRAN, K ;
SHEU, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6203-6214