Intramolecular cycloadditions of nitrones derived from 1-allyl-2-pyrrolecarbaldehyde as a route to racemic and enantiopure pyrrolizidines and indolizidines

被引:37
作者
Arnone, A
Broggini, G
Passarella, D
Terraneo, A
Zecchi, G
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy
关键词
D O I
10.1021/jo9810415
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A version of the intramolecular nitrone cycloaddition strategy, using 2-pyrrolecarbaldehyde as starting material, has been developed to synthesize new pyrrolizidines and indolizidines structurally related to biologically active alkaloids. The target molecules have been accessible in racemic as well as enantiopure form.
引用
收藏
页码:9279 / 9284
页数:6
相关论文
共 46 条
[21]  
GRUNANGER P, 1991, ISOXAZOLES, P679
[22]   INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].
GRUTERS, RA ;
NEEFJES, JJ ;
TERSMETTE, M ;
DEGOEDE, REY ;
TULP, A ;
HUISMAN, HG ;
MIEDEMA, F ;
PLOEGH, HL .
NATURE, 1987, 330 (6143) :74-77
[23]  
Hall A, 1997, SYNLETT, P123
[24]   SYNTHETIC METHODS .40. A SYNTHESIS OF (-) SUPINIDINE AND ITS REGIOISOMER BY INTRAMOLECULAR OXIME OLEFIN CYCLOADDITION [J].
HASSNER, A ;
SINGH, S ;
SHARMA, R ;
MAURYA, R .
TETRAHEDRON, 1993, 49 (11) :2317-2324
[25]   CYCLOADDITIONS .46. THERMALLY INDUCED INTRAMOLECULAR OXIME OLEFIN CYCLOADDITIONS (IOOC) LEADING TO N-BRIDGEHEAD SYSTEMS - STEREOCHEMISTRY AND MOLECULAR MECHANICS CALCULATIONS [J].
HASSNER, A ;
MAURYA, R ;
PADWA, A ;
BULLOCK, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2775-2781
[26]   CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .4. SYNTHESIS OF A TETRAHYDROXYINDOLIZIDINE THROUGH A CYCLIC NITRONE PREPARED FROM D-XYLOSE [J].
HERCZEGH, P ;
KOVACS, I ;
SZILAGYI, L ;
VARGA, T ;
DINYA, Z ;
SZTARICSKAI, F .
TETRAHEDRON LETTERS, 1993, 34 (07) :1211-1214
[27]   STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B [J].
HOLMES, AB ;
SMITH, AL ;
WILLIAMS, SF ;
HUGHES, LR ;
LIDERT, Z ;
SWITHENBANK, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1393-1405
[28]   TOTAL SYNTHESIS OF (+)-MONOMORINE-I VIA NITRONE CYCLOADDITION ROUTE [J].
ITO, M ;
KIBAYASHI, C .
TETRAHEDRON, 1991, 47 (45) :9329-9350
[29]   (5Z,8E)-3-HEPTYL-5-METHYLPYRROLIZIDINE FROM A THIEF ANT [J].
JONES, TH ;
BLUM, MS ;
FALES, HM ;
THOMPSON, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4778-4780