Formal intramolecular [5+2] photocycloaddition reactions of maleimides: A novel approach to the CDE ring skeleton of (-)-cephalotaxine

被引：22

作者：

Booker-Milburn, KI

Dudin, LF

Anson, CE

Guile, SD

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England

[3] AstraZeneca R&D Charnwood, Loughborough LE11 5RH, Leics, England

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 19期

关键词：

D O I：

10.1021/ol016411h

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

[GRAPHICS] A concise approach to the cephalotaxine CDE ring skeleton based on the intramolecular formal [5 + 2] photocycloaddition of cyclopentenyl-substituted maleimides is described. An investigation of the diatereoselectivity afforded by various protected alkoxy groups demonstrated that the best selectivity (3.5:1) was afforded by the free hydroxyl group, strongly suggesting a hydrogen-bonded excited state.

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页码：3005 / 3008

页数：4

相关论文

共 22 条

[1]

Inhibitors of bacterial signal peptidase: A series of 6-(substituted oxyethyl)penems [J].

Allsop, A ;

Brooks, G ;

Edwards, PD ;

Kaura, AC ;

Southgate, R .

JOURNAL OF ANTIBIOTICS, 1996, 49 (09) :921-928

[2]

CRYSTAL AND MOLECULAR-STRUCTURE OF CEPHALOTAXINE [J].

ARORA, SK ;

BATES, RB ;

GRADY, RA ;

GERMAIN, G ;

DECLERCQ, JP ;

POWELL, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (03) :551-554

[3]

Enantioselective intermolecular [2+2]-photocycloaddition reactions of alkenes and a 2-quinolone in solution [J].

Bach, T ;

Bergmann, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11525-11526

[4]

High facial diastereoselectivity in the photocycloaddition of a chiral aromatic aldehyde and an enamide induced by intermolecular hydrogen bonding [J].

Bach, T ;

Bergmann, H ;

Harms, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) :10650-10651

[5]

Photocycloaddition of N-4-alkenyl substituted unsaturated imides [J].

Booker-Milburn, KI ;

Costin, NJ ;

Dainty, RF ;

Patel, D ;

Sharpe, A .

TETRAHEDRON LETTERS, 1998, 39 (40) :7423-7426

[6]

Booker-Milburn KI, 2001, EUR J ORG CHEM, V2001, P1473

[7]

CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].

CHAN, TH ;

BROWNBRIDGE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538

[8]

MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].

EIS, MJ ;

WROBEL, JE ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694

[9]

PREPARATION OF CHIRAL ALLYLIC ALCOHOLS USING RHIZOPUS-NIGRICANS - USE OF THE HARADA-NAKANISHI EXCITON CHIRALITY METHOD FOR VERIFYING CONFIGURATIONAL ASSIGNMENTS OF ALLYLIC ALCOHOLS [J].

ITO, S ;

KASAI, M ;

ZIFFER, H ;

SILVERTON, JV .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (03) :574-582

[10]

Enantioselective synthesis of the ester side chain of homoharringtonine [J].

Keller, L ;

Dumas, F ;

d'Angelo, J .

TETRAHEDRON LETTERS, 2001, 42 (10) :1911-1913