Pyrrolizidine alkaloids. A concise entry to (-)-pyrrolam A

被引:23
作者
Giovenzana, GB
Sisti, M
Palmisano, G
机构
[1] DIPARTIMENTO SCI & TECNOL FARMACO,TURIN,ITALY
[2] DIPARTIMENTO CHIM ORGAN & IND,MILAN,ITALY
关键词
D O I
10.1016/S0957-4166(97)00010-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of (-)-pyrrolam A starting from (R)-prolinol is described. The key step is the dehydrative alkylation of a conveniently protected (R)-prolinol with triethyl methanetricarboxylate under the conditions of the Mitsunobu reaction. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:515 / 518
页数:4
相关论文
共 15 条
[1]   CONTRIBUTION TO ASYMMETRIC SYNTHESIS OF BICYCLIC COMPOUNDS CATALYZED BY OPTICALLY-ACTIVE AMINO-ACIDS - SYNTHESIS OF (S)-2-PYRROLIDINEPROPIONIC ACID AND (R)-4-AMINO-5-PHENYLVALERIC ACID [J].
BUCHSCHACHER, P ;
CASSAL, JM ;
FURST, A ;
MEIER, W .
HELVETICA CHIMICA ACTA, 1977, 60 (08) :2747-2755
[2]   Dehydrative alkylation of alcohols with triethyl methanetricarboxylate under Mitsunobu conditions [J].
Cravotto, G ;
Giovenzana, GB ;
Sisti, M ;
Palmisano, G .
TETRAHEDRON, 1996, 52 (40) :13007-13016
[3]   INTRAMOLECULAR HOMOCONJUGATE ADDITION - SIMPLE ENTRY TO FUNCTIONALIZED PYRROLIZIDINES AND INDOLIZIDINES [J].
DANISHEF.S ;
DYNAK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1979-1980
[4]   THE MITSUNOBU REACTION OF SOME INDAN AMINO-ALCOHOLS [J].
FREEDMAN, J ;
VAAL, MJ ;
HUBER, EW .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :670-672
[5]   A synthesis of pyrrolizidine [J].
Galinovsky, F ;
Reichard, A .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1944, 77 (02) :138-140
[6]  
GROTE R, 1990, LIEBIGS ANN CHEM, P525
[7]  
Hughes D. L., 1996, ORG PREP P INT, V28, P129
[8]  
Mattock A. R, 1986, Chemistry and Toxicology of Pyrrolizidine Alkaloids, V1st
[9]   AN ASYMMETRIC APPROACH TO THE PYRROLIZIDINE RING-SYSTEM VIA N-ACETYL AND N-PROPIONYL ANION CYCLIZATION PROCESSES [J].
MURRAY, A ;
PROCTOR, GR ;
MURRAY, PJ .
TETRAHEDRON LETTERS, 1995, 36 (02) :291-294
[10]  
PELLEGATA R, 1978, SYNTHESIS-STUTTGART, P614