New asymmetric transformation of optically active allene-1,3-dicarboxylate and its application to the formal asymmetric synthesis of (-)-epibatidine

被引：38

作者：

Node, M ^{[1
]}

Nishide, K ^{[1
]}

Fujiwara, T ^{[1
]}

Ichihashi, S ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 21期

关键词：

D O I：

10.1039/a806477f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new efficient synthesis of di-(-)-L-menthyl (R)-allene-1,3-dicarboxylate [(R)-1] involving asymmetric transformation through epimerization-crystallization with the assistance of a catalytic amount of Et3N was developed; the highly endo-selective asymmetric Diels-Alder reaction of (R)-1 with N-Boc-pyrrole for the asymmetric synthesis of 7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]heptan-2-one [(-)-6], a synthetic intermediate of (-)-epibatidine, is described.

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页码：2363 / 2364

页数：2

相关论文

共 31 条

[1]

ALBERTINI E, 1997, TETRAHEDRON, V53, P177

[2] Asymmetric total synthesis of (-)-epibatidine [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

TETRAHEDRON LETTERS, 1998, 39 (25) :4513-4516

[3] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF (R)-3-AMINO-2,3,4,5-TETRAHYDRO-1H-[1]BENZAZEPIN-2-ONE [J].

ARMSTRONG, JD ;

ENG, KK ;

KELLER, JL ;

PURICK, RM ;

HARTNER, FW ;

CHOI, WB ;

ASKIN, D ;

VOLANTE, RP .

TETRAHEDRON LETTERS, 1994, 35 (20) :3239-3242

[4] PREPARATION OF OPTICALLY-ACTIVE (R)-ALLENE-1,3-DICARBOXYLATES AND (S)-ALLENE-1,3-DICARBOXYLATES AND THEIR ASYMMETRIC CYCLOADDITION REACTIONS WITH CYCLOPENTADIENE [J].

ASO, M ;

IKEDA, I ;

KAWABE, T ;

SHIRO, M ;

KANEMATSU, K .

TETRAHEDRON LETTERS, 1992, 33 (39) :5787-5790

[5] NOTE ON THE SYNTHESIS OF AN OPTICALLY-ACTIVE ACE INHIBITOR WITH AMINO-OXO-BENZAZEPINE-1-ALKANOIC-ACID STRUCTURE BY MEANS OF AN ENANTIOCONVERGENT CRYSTALLIZATION-BASED RESOLUTION [J].

BOYER, SK ;

PFUND, RA ;

PORTMANN, RE ;

SEDELMEIER, GH ;

WETTER, HF .

HELVETICA CHIMICA ACTA, 1988, 71 (02) :337-343

[6] Chirospecific syntheses of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation [J].

Campbell, JA ;

Rapoport, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6313-6325

[7] NEW ASYMMETRIC TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS WITH (+)-TARTARIC ACID [J].

CLARK, JC ;

PHILLIPPS, GH ;

STEER, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :475-481

[8] Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route [J].

Clive, DLJ ;

Yeh, VSC .

TETRAHEDRON LETTERS, 1998, 39 (27) :4789-4792

[9] TOTAL SYNTHESIS AND DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF EPIBATIDINE [J].

FLETCHER, SR ;

BAKER, R ;

CHAMBERS, MS ;

HERBERT, RH ;

HOBBS, SC ;

THOMAS, SR ;

VERRIER, HM ;

WATT, AP ;

BALL, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1771-1778

[10]

Giblin GMP, 1997, SYNLETT, P589

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