SYNTHESES OF STRYCHNOS-TYPE AND ASPIDOSPERMATAN-TYPE ALKALOIDS .5. TOTAL SYNTHESES OF (+/-)-ECHITAMIDINE AND 20-EPI- AND 19-EPI-20-EPI-ECHITAMIDINE

被引：22

作者：

KUEHNE, ME

BROOK, CS

FRASIER, DA

XU, F

机构：

[1] Department of Chemistry, University of Vermont, Burlington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期

关键词：

D O I：

10.1021/jo00099a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Diels-Alder reactions, at two stages in the reaction sequence, provided total syntheses of the racemate of the hypotensive alkaloid echitamidine (8) and of its C-19,20 and C-20 epimers 9a and 9b.

引用

页码：5977 / 5982

页数：6

共 8 条

[1] PHENYLSELENOACETALDEHYDE, A USEFUL REAGENT FOR THE HOMOLOGATIVE CONVERSION OF HALIDES TO PHENYLSELENOMETHYL KETONES [J].

BAUDAT, R ;

PETRZILKA, M .

HELVETICA CHIMICA ACTA, 1979, 62 (05) :1406-1410

[2] A NEW, GENERAL SYNTHETIC PATHWAY TO STRYCHNOS INDOLE ALKALOIDS - 1ST TOTAL SYNTHESIS OF (+/-)-ECHITAMIDINE [J].

BONJOCH, J ;

SOLE, D ;

BOSCH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (05) :2064-2065

[3]

KELLY TR, 1984, TETRAHEDRON, V40, P4569

[4]

Kuehne M. E., 1994, NAT PROD LETT, V4, P65

[5] STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .9. 2 TOTAL SYNTHESES OF MINOVINCINE [J].

KUEHNE, ME ;

EARLEY, WG .

TETRAHEDRON, 1983, 39 (22) :3707-3714

[6] TOTAL SYNTHESES OF TUBOTAIWINE AND 19,20-DIHYDRO-20-EPI-AKUAMMICINE [J].

KUEHNE, ME ;

FRASIER, DA ;

SPITZER, TD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2696-2700

[7]

TAYLOR WI, 1965, EXPERIENTIA, V21, P5008

[8] THE STRUCTURE OF ECHITAMIDINE, A STEREOISOMER AND 2 REGIOISOMERS [J].

ZECHES, M ;

RAVAO, T ;

RICHARD, B ;

MASSIOT, G ;

LEMENOLIVIER, L ;

GUILHEM, J ;

PASCARD, C .

TETRAHEDRON LETTERS, 1984, 25 (06) :659-662

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