Synthesis of enantiopure 3-azabicyclo[3.3.0]octen-7-one derivatives via intramolecular Pauson-Khand cycloaddition reaction using tri-O-acetyl-D-glucal as starting material

被引：8

作者：

Areces, P ^{[1
]}

Durán, MA

Plumet, J

Hursthouse, MB

Light, ME

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, Badajoz 28071, Spain

[2] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[3] Univ Southampton, Dept Chem, Southampton S017 1BJ, Hants, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 10期

关键词：

D O I：

10.1021/jo011129+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some N-substituted-3-azabicyclo[3.3.0]octen-7-one derivatives have been synthesized in an enantiomerically pure form starting from tri-O-acetyl-D-glucal via intramolecular Pauson-Khand (IPK) cycloaddition.

引用

页码：3506 / 3509

页数：4

共 32 条

[1] Base-induced bridge cleavage of 1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene derivatives:: A short synthesis of an advanced intermediate for the A and C ring subunits of taxol [J].

Arjona, O ;

León, M ;

Plumet, J .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :272-275

[2] Enantioselective total synthesis of (-)-α-kainic acid [J].

Bachi, MD ;

Melman, A .

PURE AND APPLIED CHEMISTRY, 1998, 70 (02) :259-262

[3] SYNTHESIS OF N-BOC-3-AZABICYCLO[3.3.0]OCTAN-7-ONE VIA REDUCTIVE PAUSON-KHAND CYCLIZATION AND SUBSEQUENT CONVERSION TO A NOVEL DIAZATRICYCLIC RING-SYSTEM [J].

BECKER, DP ;

FLYNN, DL .

TETRAHEDRON, 1993, 49 (23) :5047-5054

[4] STUDIES OF THE SOLID-PHASE PAUSON-KHAND REACTION - SELECTIVE INSITU ENONE REDUCTION TO 3-AZABICYCLO[3.3.0]OCTANONES [J].

BECKER, DP ;

FLYNN, DL .

TETRAHEDRON LETTERS, 1993, 34 (13) :2087-2090

[5] THE SYNTHESIS OF NITROGEN-HETEROCYCLES VIA THE INTRAMOLECULAR KHAND REACTION - FORMATION OF TETRA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXAHYDRO-6H-2-PYRINDIN-6-ONES [J].

BROWN, SW ;

PAUSON, PL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1205-1209

[6]

de Meijere A, 2000, ANGEW CHEM INT EDIT, V39, P3964, DOI 10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO

[7]

2-C

[8] Applications of stoichiometric transition metal complexes in organic synthesis [J].

Fletcher, AJ ;

Christie, SDR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (01) :1-13

[9] Cobalt mediated cyclisations [J].

Fletcher, AJ ;

Christie, SDR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (11) :1657-1668

[10]

GLEIS O, 1998, ANGEW CHEM INT EDIT, V37, P911

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