Ring-opening aminolysis of sesquiterpene lactones: An easy entry to bioactive sesquiterpene derivatives. Synthesis of (+)-beta-cyperone and (-)-eudesma-3,5-diene from santonin.

被引：18

作者：

Blay, G ^{[1
]}

Cardona, L ^{[1
]}

Garcia, B ^{[1
]}

Garcia, CL ^{[1
]}

Pedro, JR ^{[1
]}

机构：

[1] UNIV VALENCIA,FAC QUIM,DEPT QUIM ORGAN,E-46100 BURJASSOT,VALENCIA,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 31期

关键词：

D O I：

10.1016/0040-4020(96)00571-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Santonin (1) and other sesquiterpene lactones (2-3) react with pyrrolidine and other cyclic secondary amines to afford gamma-hydroxyamides, which by elimination with mesyl chloride in pyridine-benzene at 80 degrees C give unsaturated amides 4a-4c, 5a-5c and 6. Starting from amides 5a-5c a series of bioactive compounds against Locusta migratoria have been prepared, differing in the oxidation states of the C-3 and C-12 carbon atoms. Starting from amides 5a and 6 two conjugated diene eudesmanes (+)-beta-cyperone (15) and (-)eudesma-3,5-diene (19) have been prepared involving an elaboration of the amide group of the side chain of the eudesmane skeleton. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：10507 / 10518

页数：12

共 20 条

[1]

BASHA A, 1977, TETRAHEDRON LETT, V48, P4171

[2] A NONCATALYZED RING-OPENING AMINOLYSIS REACTION OF SESQUITERPENE LACTONES [J].

BLAY, G ;

CARDONA, L ;

GARCIA, B ;

GARCIA, CL ;

PEDRO, JR .

TETRAHEDRON LETTERS, 1994, 35 (06) :931-934

[3]

BORCH RF, 1968, TETRAHEDRON LETT, V1, P61

[4]

CASTILLO M, 1995, 6 INT C JUV HORM WOO

[5]

CHA JS, 1992, B KOR CHEM SOC, V13, P670

[6] THE USE OF MICROWAVE-OVENS FOR RAPID ORGANIC-SYNTHESIS [J].

GEDYE, R ;

SMITH, F ;

WESTAWAY, K ;

ALI, H ;

BALDISERA, L ;

LABERGE, L ;

ROUSELL, J .

TETRAHEDRON LETTERS, 1986, 27 (03) :279-282

[7]

GREENE AE, 1971, TETRAHEDRON LETT, V44, P4147

[8]

Gyoung Y. S, 1991, J KOREAN CHEM SOC, V35, P296

[9]

Heathcock C. L., 1983, TOTAL SYNTHESIS NATU, V5

[10]

HEATHCOCK CH, 1973, TOTAL SYNTHESIS NATU, V2, pCH2

← 1 2 →