Transannular dipolar cycloaddition as an approach towards the synthesis of the core ring system of the sarain alkaloids

被引：16

作者：

Franklin, Andrew I. ^{[1
]}

Bensa, David ^{[1
]}

Adams, Harry ^{[1
]}

Coldham, Iain ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; TRICYCLIC CORE; ASYMMETRIC CONSTRUCTION; CLOSING METATHESIS; AZOMETHINE YLIDES; A CORE; INTERMEDIATE; SKELETON;

D O I：

10.1039/c0ob01019g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular transannular dipolar cycloaddition was investigated as a key step in a synthetic approach to the core of the sarain alkaloids; although the use of an azomethine ylide was unsuccessful with the chosen aldehyde substrate, cycloaddition with a nitrone did give the alternative regioisomeric bridged cycloadduct.

引用

页码：1901 / 1907

页数：7

共 39 条

[1] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .19. INTRAMOLECULAR CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE YLIDES GENERATED VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS [J].

ARDILL, H ;

GRIGG, R ;

SRIDHARAN, V ;

SURENDRAKUMAR, S .

TETRAHEDRON, 1988, 44 (15) :4953-4966

[2] Total synthesis of (-)-Sarain A [J].

Becker, Michael H. ;

Chua, Peter ;

Downham, Robert ;

Douglas, Christopher J. ;

Garg, Neil K. ;

Hiebert, Sheldon ;

Jaroch, Stefan ;

Matsuoka, Richard T. ;

Middleton, Joy A. ;

Ng, Fay W. ;

Overman, Larry E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11987-12002

[3] Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents [J].

Bensa, David ;

Coldham, Iain ;

Feinaeugle, Pia ;

Pathaka, Ravindra B. ;

Butlin, Roger J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (08) :1410-1415

[4]

Burrell AJM, 2010, CURR ORG SYNTH, V7, P312

[5] SELECTED BIOLOGICAL-ACTIVITIES OF SARAINES [J].

CAPRIOLI, V ;

CIMINO, G ;

DEGIULIO, A ;

MADAIO, A ;

SCOGNAMIGLIO, G ;

TRIVELLONE, E .

COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1992, 103 (01) :293-296

[6] Formation of medium-ring heterocycles by diene and enyne metathesis [J].

Chattopadhyay, Shital K. ;

Karmakar, Swastik ;

Biswas, Titas ;

Majumdar, K. C. ;

Rahaman, H. ;

Roy, B. .

TETRAHEDRON, 2007, 63 (19) :3919-3952

[7] STRUCTURAL STUDIES ON SARAINE-A [J].

CIMINO, G ;

SCOGNAMIGLIO, G ;

SPINELLA, A ;

TRIVELLONE, E .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06) :1519-1525

[8]

CIMINO G, 1986, B SOC CHIM BELG, V95, P783

[9] UNPRECEDENTED ALKALOID SKELETON FROM THE MEDITERRANEAN SPONGE RENIERA-SARAI - X-RAY STRUCTURE OF AN ACETATE DERIVATIVE OF SARAIN-A [J].

CIMINO, G ;

MATTIA, CA ;

MAZZARELLA, L ;

PULITI, R ;

SCOGNAMIGLIO, G ;

SPINELLA, A ;

TRIVELLONE, E .

TETRAHEDRON, 1989, 45 (12) :3863-3872

[10] Dipolar cycloaddition and ring-closing metathesis in the synthesis of the tetracyclic ABCE ring system of manzamine A [J].

Coldham, I ;

Pih, SM ;

Rabot, R .

SYNLETT, 2005, (11) :1743-1745

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