Intramolecular amidomercurations under allylic control:: a stereoselective synthesis of (+)-pseudohygroline and (+)-3-hydroxypyrrolizidine

被引：9
作者：
Enierga, G
Espiritu, M
Perlmutter, P
Pham, N
Rose, M
Sjöberg, S
Thienthong, N
Wong, K
机构：
[1] Monash Univ, Dept Chem, Clayton, Vic 3800, Australia
[2] Uppsala Univ, Dept Organ Chem, Uppsala, Sweden
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
D O I：
10.1016/S0957-4166(01)00064-7
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The diastereoselectivity of intramolecular amidomercurations can be reversed by altering the remote allylic substituent of omega -alkenylcarbamates. This methodology has been applied to the synthesis of (+)-pseudohygroline and (+)-3-hydroxypyrrolizidine. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码：597 / 604
页数：8
相关论文
共 24 条
[1]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[2]   Remote allylic silyloxy groups as stereocontrol elements in intramolecular oxymercurations of gamma-hydroxyalkenes [J].
Bratt, K ;
Garavelas, A ;
Perlmutter, P ;
Westman, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2109-2117
[3]   SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .27. ENANTIOSELECTIVE TOTAL SYNTHESIS OF EITHER ENANTIOMER OF THE ANTIFUNGAL ANTIBIOTIC PREUSSIN (L-657,398) FROM (S)-PHENYLALANINE [J].
DENG, W ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11241-11250
[4]   SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .14. TOTAL SYNTHESIS OF (+)-ARISTOLONE [J].
DOBLER, M ;
BORSCHBERG, HJ .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :2025-2032
[5]   An enantioselective synthesis of (+)-pseudohygroline. [J].
Enierga, G ;
Hockless, DCR ;
Perlmutter, P ;
Rose, M ;
Sjöberg, S ;
Wong, K .
TETRAHEDRON LETTERS, 1998, 39 (18) :2813-2814
[6]   STEREOSELECTIVE SYNTHESIS OF TETRAHYDROFURANS USING INTRAMOLECULAR OXYMERCURATIONS [J].
GARAVELAS, A ;
MAVROPOULOS, I ;
PERLMUTTER, P ;
WESTMAN, G .
TETRAHEDRON LETTERS, 1995, 36 (03) :463-466
[7]  
GELAS J, 1981, HETEROCYCLES, V16, P1587
[8]  
GENARD S, 1991, B SOC CHIM FR, P397
[9]   PYRROLIZIDINES VIII - H-1-NMR SPECTRA OF 1-(BS)-HEXAHYDRO-PYRROLIZIN ONE AND 2-(8S)-HEXAHYDRO-PYRROLIZIN-ONE AND OF THE DIASTEREOMERIC 1-(8S)-HEXAHYDRO-PYRROLIZIN-OLES AND 2-(8S)-HEXAHYDRO-PYRROLIZIN-OLES - STEREOCHEMISTRY OF THE BICYCLUS [J].
GUNDERMANN, H ;
WOLFF, C ;
SCHNEKENBURGER, J .
ARCHIV DER PHARMAZIE, 1988, 321 (11) :799-802
[10]   APPLICATIONS OF INTRAMOLECULAR AMIDOMERCURATION .2. SYNTHESIS OF "TRANS-5-HYDROXY-2-PROPYLPIPERIDINE, (+/-)-PSEUDOCONHYDRINE [J].
HARDING, KE ;
BURKS, SR .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01) :40-44
123