Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer supported reagents

被引：117

作者：

Habermann, J ^{[1
]}

Ley, SV ^{[1
]}

Scott, JS ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 10期

关键词：

D O I：

10.1039/a901802f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ten-step synthesis of (+/-)-epibatidine 1 is described, using an organised array of polymer supported reagents and sequestering agents in a successive manner. No chromatographic purification steps are required to afford the product in >90% purity.

引用

页码：1253 / 1255

页数：3

共 38 条

[1] Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine
Albertini, E
Barco, A
Benetti, S
DeRisi, C
Pollini, GP
Zanirato, V
[J]. TETRAHEDRON LETTERS, 1997, 38 (04) : 681 - 684
[2] TOTAL SYNTHESIS OF (+/-)-EPIBATIDINE
ALBERTINI, E
BARCO, A
BENETTI, S
DERISI, C
POLLINI, GP
ROMAGNOLI, R
ZANIRATO, V
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9297 - 9300
[3] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile
Aoyagi, S
Tanaka, R
Naruse, M
Kibayashi, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8397 - 8406
[4] Avenoza A, 1998, SYNTHESIS-STUTTGART, P1335
[5] Barrett A.G.M., 1988, TETRAHEDRON LETT, V29, P5733
[6] The effect of DMSO on the borohydride reduction of a cyclohexanone: A formal enantioselective synthesis of (+)-epibatidine.
Barros, MT
Maycock, CD
Ventura, MR
[J]. TETRAHEDRON LETTERS, 1999, 40 (03) : 557 - 560
[7] TOTAL SYNTHESIS OF EPIBATIDINE
BROKA, CA
[J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3251 - 3254
[8] Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives
Cabanal-Duvillard, I
Berrien, JF
Royer, J
Husson, HP
[J]. TETRAHEDRON LETTERS, 1998, 39 (29) : 5181 - 5184
[9] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
Caldarelli, M
Habermann, J
Ley, SV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02): : 107 - 110
[10] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE
COREY, EJ
LOH, TP
ACHYUTHARAO, S
DALEY, DC
SARSHAR, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5600 - 5602

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