An epoxide rearrangement-radical rearrangement approach to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes: Synthesis of an epibatidine analogue

被引：27

作者：

Hodgson, DM

Maxwell, CR

Matthews, IR

机构：

[1] Univ Oxford, Dept Chem, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Zeneca Agrochem, Jealotts Hill Res Stn, Bracknell RG42 6ET, Berks, England

来源：

SYNLETT | 1998年 / 12期

关键词：

epoxide; rearrangement; radical deoxygenation; epibatidine;

D O I：

10.1055/s-1998-1963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-induced isomerisation of epoxide 9 gives an azanortricyclanol 10 which is a precursor for a novel free-radical induced rearrangement to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes 14a-c; 14c (R = 6-chloro-3-pyridinyl) is converted to the epibatidine analogue 2.

引用

页码：1349 / 1350

页数：2

共 19 条

[1] Evidence that a dioxirane is not responsible for alkene epoxidation in a ketone-Oxone(R) system
Armstrong, A
Clarke, PA
Wood, A
[J]. CHEMICAL COMMUNICATIONS, 1996, (07) : 849 - 850
[2] Broad-spectrum, non-opioid analgesic activity by selective modulation of neuronal nicotinic acetylcholine receptors
Bannon, AW
Decker, MW
Holladay, MW
Curzon, P
Donnelly-Roberts, D
Puttfarcken, PS
Bitner, RS
Diaz, A
Dickenson, AH
Porsolt, RD
Williams, M
Arneric, SP
[J]. SCIENCE, 1998, 279 (5347) : 77 - 81
[3] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
MCCOMBIE, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
[4] BLONDET D, 1982, HETEROCYCLES, V19, P2155
[5] SYNTHESIS AND MUSCARINIC RECEPTOR ACTIVITY OF ESTER DERIVATIVES OF 2-SUBSTITUTED 2-AZABICYCLO[2.2.1]HEPTAN-5-OL AND 2-ABZABICYCLO[2.2.1]HEPTAN-6-OL
CARROLL, FI
ABRAHAM, P
CHEMBURKAR, S
HE, XC
MASCARELLA, SW
KWON, YW
TRIGGLE, DJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (12) : 2184 - 2191
[6] Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes
Chen, ZM
Trudell, ML
[J]. CHEMICAL REVIEWS, 1996, 96 (03) : 1179 - 1193
[7] THE EPIBATIDINE COMPETITION - SYNTHETIC WORK ON A NOVEL NATURAL ANALGESIC
DEHMLOW, EV
[J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1995, 337 (03): : 167 - 174
[8] A NEW METHOD FOR THE DEOXYGENATION OF TERTIARY AND SECONDARY ALCOHOLS
DOLAN, SC
MACMILLAN, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) : 1588 - 1589
[9] EVIDENCE FOR HYDROGEN ABSTRACTION BY CLASSICAL RADICALS IN NORBORNENYL-NORTRICYCLYL SYSTEM
HALGREN, TA
FIRKINS, JL
FUJIMOTO, TA
SUZUKAWA, HH
ROBERTS, JD
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1971, 68 (12) : 3216 - &
[10] Isomerisations of cycloalkene- and bicycloalkene-derived achiral epoxides by enantioselective α-deprotonation
Hodgson, DM
Lee, GP
Marriott, RE
Thompson, AJ
Wisedale, R
Witherington, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (14): : 2151 - 2161

← 1 2 →