The synthesis of (+/-)-heliotridane and (6S,7S)-dihydroxyheliotridane via sequential hydrogen atom abstraction and cyclisation

被引：52

作者：

Robertson, J

Peplow, MA

Pillai, J

机构：

[1] Dyson Perrins Laboratory, Oxford OX1 3QY, South Parks Road

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 32期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/0040-4039(96)01237-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of N-(3-bromo-3-butenyl)pyrrolidine derivatives with tributyltin hydride and AIBN leads to hydrogen atom transfer of the intermediate vinyl radicals to give a-amino radicals which then cyclise stereoselectively yielding pyrrolizidines 1 and 13. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：5825 / 5828

页数：4

共 25 条

[1] ADAMS ROGER, 1941, JOUR AMER CHEM SOC, V63, P228, DOI 10.1021/ja01846a054
[2] ARAKAWA Y, 1991, CHEM PHARM BULL, V39, P2219
[3] STEREOSELECTIVITY OF RING-CLOSURE OF SUBSTITUTED HEX-5-ENYL RADICALS
BECKWITH, ALJ
LAWRENCE, T
SERELIS, AK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) : 484 - 485
[4] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
BECKWITH, ALJ
[J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
[5] SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE
CORDERO, FM
CICCHI, S
GOTI, A
BRANDI, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (06) : 949 - 952
[6] TRANSLOCATION OF RADICAL SITES BY INTRAMOLECULAR 1,5-HYDROGEN ATOM TRANSFER
CURRAN, DP
KIM, D
LIU, HT
SHEN, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) : 5900 - 5902
[7] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES
CURRAN, DP
CHANG, CT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) : 3140 - 3157
[8] STEREOSELECTIVE SYNTHESIS OF (+)-LENIGINOSINE AND (-)-LENTIGINOSINE
GURJAR, MK
GHOSH, L
SYAMALA, M
JAYASREE, V
[J]. TETRAHEDRON LETTERS, 1994, 35 (47) : 8871 - 8872
[9] NEW METHODS FOR ALKALOID SYNTHESIS - ALPHA-ACYLAMINO RADICAL CYCLIZATIONS
HART, DJ
TSAI, YM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) : 1430 - 1432
[10] Hartmann T., 1995, Alkaloids: Chemical and biological perspectives, P155, DOI DOI 10.1016/B978-0-08-042089-9.50011-5

← 1 2 3 →