Synthesis of the tricyclic core of sarain A. Use of formaldehyde in an intramolecular Grigg azomethine ylide cyclization

被引：70

作者：

Denhart, DJ ^{[1
]}

Griffith, DA ^{[1
]}

Heathcock, CH ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 26期

关键词：

D O I：

10.1021/jo981801b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[No abstract available]

引用

页码：9616 / 9617

页数：2

共 15 条

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

CIMINO, G ;

SCOGNAMIGLIO, G ;

SPINELLA, A ;

TRIVELLONE, E .

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

[2] 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

[3] Asymmetric construction of the diazatricyclic core of the marine alkaloids sarains A-C [J].

Downham, R ;

Ng, FW ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8096-8097

[4] PROGRESS TOWARD THE SYNTHESIS OF SARAIN-A - AN UNANTICIPATED REARRANGEMENT [J].

GRIFFITH, DA ;

HEATHCOCK, CH .

TETRAHEDRON LETTERS, 1995, 36 (14) :2381-2384

[5] PROTOTROPIC ROUTES TO 1,3-DIPOLES AND 1,5-DIPOLES, AND 1,2-YLIDES - APPLICATIONS TO THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].

GRIGG, R .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (01) :89-121

[6] Structural and stereochemical studies of saraines: Macrocyclic alkaloids of the sponge Reniera sarai [J].

Guo, YW ;

Madaio, A ;

Trivellone, E ;

Scognamiglio, G ;

Cimino, G .

TETRAHEDRON, 1996, 52 (24) :8341-8348

[7]

HEATHCOCK CH, 1995, SYNLETT, P467

[8] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF STABILIZED AZOMETHINE YLIDES TO UNACTIVATED DIPOLAROPHILES [J].

HENKE, BR ;

KOUKLIS, AJ ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7056-7066

[9] AZOMETHINE YLIDS FROM DIETHYL AMINOMALONATE [J].

HUSINEC, S ;

SAVIC, V ;

PORTER, AEA .

TETRAHEDRON LETTERS, 1988, 29 (50) :6649-6650

[10]

IRIE O, IN PRESS J ORG CHEM

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