Application of an organozinc reagent derived from (S)-pyroglutamic acid:: a formal synthesis of epibatidine

被引：28

作者：

Karstens, WFJ ^{[1
]}

Moolenaar, MJ ^{[1
]}

Rutjes, FPJT ^{[1
]}

Grabowska, U ^{[1
]}

Speckamp, WN ^{[1
]}

Hiemstra, H ^{[1
]}

机构：

[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

epibatidine; organozinc reagent; N-acyliminium ions; azabicylo[2.2.1]heptanes;

D O I：

10.1016/S0040-4039(99)01808-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal total synthesis of natural (-)-epibatidine has been developed. Key steps in the synthesis are a copper(I)-mediated coupling of an (S)-pyroglutamic acid-derived organozine reagent with 1-iodo-3-trimethylsilyl-1-propyne and an N-acyl- or N-sulfonyliminium ion cyclization, Following this route, various N-protected hydroxylactams were converted into 7-azabicylo[2,2,1]heptane derivatives, (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8629 / 8632

页数：4

共 52 条

[1] APPROACHES TO THE SYNTHESIS OF CYTOCHALASANS .9. A VERSATILE CONCEPT LEADING TO ALL STRUCTURAL TYPES OF CYTOCHALASANS [J].

ACKERMANN, J ;

MATTHES, M ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1990, 73 (01) :122-132

[2] A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo[2.2.1]heptane ring systems from D(-)-quinic acid: Application to the formal syntheses of (-)-balanol and (-)-epibatidine [J].

Albertini, E ;

Barco, A ;

Benetti, S ;

DeRisi, C ;

Pollini, GP ;

Zanirato, V .

TETRAHEDRON, 1997, 53 (50) :17177-17194

[3] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8397-8406

[4]

Avenoza A, 1998, SYNTHESIS-STUTTGART, P1335

[5]

BADIO B, 1994, MOL PHARMACOL, V45, P563

[6]

BADIO B, 1994, MED CHEM RES, V4, P440

[7] Broad-spectrum, non-opioid analgesic activity by selective modulation of neuronal nicotinic acetylcholine receptors [J].

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 .

SCIENCE, 1998, 279 (5347) :77-81

[8] IMPROVED PROCEDURES FOR BROMOPROPADIENE AND IODOPROPADIENE [J].

BRANDSMA, L ;

VERKRUIJSSE, HD .

SYNTHETIC COMMUNICATIONS, 1991, 21 (01) :69-72

[9] TOTAL SYNTHESIS OF EPIBATIDINE [J].

BROKA, CA .

TETRAHEDRON LETTERS, 1993, 34 (20) :3251-3254

[10] Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives [J].

Cabanal-Duvillard, I ;

Berrien, JF ;

Royer, J ;

Husson, HP .

TETRAHEDRON LETTERS, 1998, 39 (29) :5181-5184

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