SYNTHESIS OF (+)-ISOALANTOLACTONE AND (+)-ISOALLOALANTOLACTONE FROM (-)-SANTONIN

被引：21

作者：

BLAY, G ^{[1
]}

CARDONA, L ^{[1
]}

GARCIA, B ^{[1
]}

PEDRO, JR ^{[1
]}

SERRANO, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1992年 / 48卷 / 25期

关键词：

SANTONIN; ISOALANTOLACTONE; ISOALLOALANTOLACTONE; SYNTHESIS; FUNCTIONALITY TRANSFER;

D O I：

10.1016/S0040-4020(01)89024-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports on the chemical conversion of (-)-santonin into (+)-isoalantolactone and (+)-isoalloalantolactone involving functionality transfer from C6 to C-8, refunctionalization of the ring A and the formation of the alpha-methylene-8-beta,12-olide moiety.

引用

页码：5265 / 5272

页数：8

共 24 条

[1] CHROMOSOMAL-ABERRATIONS CAUSED BY SESQUITERPENE LACTONES IN CHINESE-HAMSTER OVARY CELLS [J].

ABEYSEKERA, BF ;

ABRAMOWSKI, Z ;

TOWERS, GHN .

BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1985, 13 (03) :365-369

[2] FUNCTIONALITY TRANSFER FROM C-6 TO C-8 IN SESQUITERPENES - SYNTHESIS OF 8-EPI-IVANGUSTIN AND 8-EPI-ISOIVANGUSTIN FROM SANTONIN [J].

BLAY, G ;

CARDONA, ML ;

GARCIA, B ;

PEDRO, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6172-6175

[3] THE CHEMISTRY OF SANTONIN .3. THE STEREOCHEMISTRY OF SOME REDUCTION PRODUCTS OF SANTONIN [J].

COCKER, W ;

MCMURRY, TBH .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4549-4557

[4]

COOPER JL, 1977, TETRAHEDRON LETT, V38, P3321

[5] TOTAL SYNTHESIS OF DIHYDROCOSTUNOLIDE [J].

COREY, EJ ;

HORTMANN, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (24) :5736-&

[6]

FISCHER NH, 1980, FORTSCHR CHEM ORG NA, V38, P47

[7] CONVERSIONS OF ALPHA-METHYL TO ALPHA-METHYLENE GAMMA-LACTONES - SYNTHESIS OF TWO ALLERGENIC SESQUITERPENE LACTONES, (-)-FRULLANOLIDE AND (+)-ARBUSCULIN B [J].

GREENE, AE ;

MULLER, JC ;

OURISSON, G .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :186-191

[8] EUDESMAN-12,8-BETA-OLIDES AND OTHER TERPENES FROM ARTEMISIA SPECIES [J].

GREGER, H ;

ZDERO, C ;

BOHLMANN, F .

PHYTOCHEMISTRY, 1986, 25 (04) :891-897

[9]

GRIECO PA, 1974, J ORG CHEM, V39, P120, DOI 10.1021/jo00915a036

[10] STEREOSTRUCTURES OF INUNAL AND ISOALLOALANTOLACTONE 2 BIOLOGICALLY-ACTIVE SESQUITERPENE LACTONES FROM INULA-RACEMOSA [J].

KAUR, B ;

KALSI, PS .

PHYTOCHEMISTRY, 1985, 24 (09) :2007-2010

← 1 2 3 →