SYNTHESIS OF THE REPORTED STRUCTURE OF HERBOLIDE-I AND ITS C-11 EPIMER FROM ARTEMISIN

被引：18

作者：

BLAY, G ^{[1
]}

CARDONA, L ^{[1
]}

GARCIA, B ^{[1
]}

PEDRO, JR ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Artemisin (1) was converted into 12 (the reported structure for herbolide I) and its C-11 epimer 19 via a synthetic pathway involving a functionality transfer from C-8 to C-9 and an A-ring refunctionalization. The H-1 and C-13 NMR data of synthetic products 12 and 19 reveal that the assigned structure of the natural herbolide I is erroneous.

引用

页码：7204 / 7208

页数：5

共 53 条

[1]

Adekenov S. M., 1992, Chemistry of Natural Compounds, V28, P387

[2] SYNTHESIS OF SOME NOVEL TRIFLUOROMETHANESULFONATES AND THEIR REACTIONS WITH ALCOHOLS [J].

BEARD, CD ;

BAUM, K ;

GRAKAUSK.V .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) :3673-3677

[3] FUNCTIONALITY TRANSFER FROM C(8) TO C(9) IN SESQUITERPENES - SYNTHESIS OF THE NAMED HERBOLIDE-E FROM ARTEMISIN [J].

BLAY, G ;

CARDONA, L ;

GARCIA, B ;

PEDRO, JR .

TETRAHEDRON LETTERS, 1992, 33 (36) :5253-5256

[4] SYNTHESIS OF (+)-ISOALANTOLACTONE AND (+)-ISOALLOALANTOLACTONE FROM (-)-SANTONIN [J].

BLAY, G ;

CARDONA, L ;

GARCIA, B ;

PEDRO, JR ;

SERRANO, A .

TETRAHEDRON, 1992, 48 (25) :5265-5272

[5] 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

[6] EUDESMANOLIDES AND COSTIC ACID-DERIVATIVES FROM FLOURENSIA-MACROPHYLLA [J].

BOHLMANN, F ;

JAKUPOVIC, J ;

SCHUSTER, A ;

KING, RM ;

ROBINSON, H .

PHYTOCHEMISTRY, 1984, 23 (07) :1445-1448

[7] NATURALLY-OCCURRING TERPENE DERIVATIVES .405. NEW GERMACRANOLIDES FROM INULA-HETEROLEPIS [J].

BOHLMANN, F ;

GOREN, NA ;

GRENZ, M .

PHYTOCHEMISTRY, 1982, 21 (05) :1166-1168

[8]

BOHLMANN F, 1982, CHEM PHARM BULL, V21, P1166

[9] TOTAL SYNTHESES OF ROTHIN-A AND ROTHIN-B [J].

CARDA, M ;

ARNO, M ;

MARCO, JA .

TETRAHEDRON, 1986, 42 (13) :3655-3662

[10] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].

CARON, M ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560

← 1 2 3 4 5 6 →