Facile and highly stereoselective synthesis of the tetracyclic erythrinane core

被引：66

作者：

Allin, SM ^{[1
]}

James, SL

Elsegood, MRJ

William, PM

机构：

[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

[2] GlaxoSmithKline Pharmaceut, Synthet Chem, Harlow CM19 5AW, Essex, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 26期

关键词：

D O I：

10.1021/jo0205661

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of the tetracyclic core of the Erythrina alkaloids is reported through the application of a Meyers bicyclic lactam. template.

引用

页码：9464 / 9467

页数：4

共 21 条

[11] ASYMMETRIC-SYNTHESIS OF BOTH ENANTIOMERS OF PYRROLIDINOISOQUINOLINE DERIVATIVES FROM L-MALIC ACID AND L-TARTARIC ACID [J].

LEE, YS ;

KANG, DW ;

LEE, SJ ;

PARK, H .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7149-7152

[12]

LETE E, 1993, SYNLETT, P41

[13] Tandem carbophilic addition-N-acyliminium ion cyclization for the synthesis of functionalized pyrrolo[2,1-a]isoquinolones: Key intermediates for the preparation of Erythrina-type alkaloids [J].

Manteca, I ;

Sotomayor, N ;

Villa, MJ ;

Lete, E .

TETRAHEDRON LETTERS, 1996, 37 (43) :7841-7844

[14] Chiral bicyclic lactams: Useful precursors and templates for asymmetric syntheses [J].

Meyers, AI ;

Brengel, GP .

CHEMICAL COMMUNICATIONS, 1997, (01) :1-8

[15] A triple cascade sequence as a strategy for the construction of the erythrinane skeleton [J].

Padwa, A ;

Hennig, R ;

Kappe, CO ;

Reger, TS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1144-1155

[16]

RAGAN JA, 1995, HETEROCYCLES, V41, P57

[17] ENDO-SELECTIVE CYCLIZATION PATHWAYS IN THE INTRAMOLECULAR HECK REACTION [J].

RIGBY, JH ;

HUGHES, RC ;

HEEG, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (29) :7834-7835

[18] Synthetic studies on the erythrina alkaloids.: Preparation of (±)-2-epi-erythrinitol [J].

Rigby, JH ;

Deur, C ;

Heeg, MJ .

TETRAHEDRON LETTERS, 1999, 40 (38) :6887-6890

[19]

Sangai M., 1994, CHEM PHARM BULL, V42, P204

[20] THE ABSOLUTE CONFIGURATION OF LIGNANS [J].

SCHRECKER, AW ;

HARTWELL, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3827-3831

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