Intramolecular cycloadditions of nitrones derived from 1-allyl-2-pyrrolecarbaldehyde as a route to racemic and enantiopure pyrrolizidines and indolizidines

被引：37

作者：

Arnone, A

Broggini, G

Passarella, D

Terraneo, A

Zecchi, G

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 25期

关键词：

D O I：

10.1021/jo9810415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A version of the intramolecular nitrone cycloaddition strategy, using 2-pyrrolecarbaldehyde as starting material, has been developed to synthesize new pyrrolizidines and indolizidines structurally related to biologically active alkaloids. The target molecules have been accessible in racemic as well as enantiopure form.

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页码：9279 / 9284

页数：6

相关论文

共 46 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .33. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES IN WHICH THE DIPOLAROPHILE IS LOCATED WITHIN THE OXIME [J].

ARMSTRONG, P ;

GRIGG, R ;

HEANEY, F ;

SURENDRAKUMAR, S ;

WARNOCK, WJ .

TETRAHEDRON, 1991, 47 (25) :4495-4518

[2] Microwave induced 1,3-dipolar cycloaddition reactions of nitrones [J].

Baruah, B ;

Prajapati, D ;

Boruah, A ;

Sandhu, JS .

SYNTHETIC COMMUNICATIONS, 1997, 27 (15) :2563-2567

[3] SYNTHESIS OF DIHYDROISOXAZOLO AND TETRAHYDROISOXAZOLO[3',4'-3,4]PYRROLO[1,2-A]INDOLES VIA INTRAMOLECULAR CYCLO-ADDITIONS - A NOVEL CLASS OF MITOMYCIN ANALOGS [J].

BHUYAN, PJ ;

BORUAH, RC ;

SANDHU, JS .

TETRAHEDRON LETTERS, 1989, 30 (11) :1421-1422

[4] NITRONES AND OXAZIRIDINES .45. FORMATION OF PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR NITRONE CYCLOADDITION [J].

BLACK, DS ;

CRAIG, DC ;

DEBDAS, RB ;

KUMAR, N .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (05) :603-622

[5] EFFICIENT ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE BUILDING-BLOCKS [J].

BOND, TJ ;

JENKINS, R ;

RIDLEY, AC ;

TAYLOR, PC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2241-2242

[6] Peracid oxidation of chiral isoxazolidines: Developments and perspectives [J].

Broggini, G ;

Zecchi, G .

TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1431-1434

[7]

CHASTANET J, 1985, HETEROCYCLES, V23, P653

[8] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR STEREOSELECTIVE SYNTHESES OF PYRROLIDINE AND PYRROLIZIDINE SYSTEMS [J].

CHIACCHIO, U ;

CASUSCELLI, F ;

CORSARO, A ;

LIBRANDO, V ;

RESCIFINA, A ;

ROMEO, R ;

ROMEO, G .

TETRAHEDRON, 1995, 51 (19) :5689-5700

[9] An asymmetric approach to pyrrolidinone and pyrrolizidinone systems by intramolecular oxime-olefin cycloaddition [J].

Chiacchio, U ;

Corsaro, A ;

Pistara, V ;

Rescifina, A ;

Romeo, G ;

Romeo, R .

TETRAHEDRON, 1996, 52 (23) :7875-7884

[10] THE TOTAL SYNTHESIS OF (+/-)-INDOLIZIDINES 235B AND 235B' [J].

COLLINS, I ;

FOX, ME ;

HOLMES, AB ;

WILLIAMS, SF ;

BAKER, R ;

FORBES, IJ ;

THOMPSON, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01) :175-182

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