Dimerization of butenolide structures.: A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)-biepiasterolide

被引：59

作者：

Bagal, SK ^{[1
]}

Adlington, RM ^{[1
]}

Baldwin, JE ^{[1
]}

Marquez, R ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 26期

关键词：

D O I：

10.1021/jo0488053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

引用

收藏

页码：9100 / 9108

页数：9

相关论文

共 32 条

[1]

Aresta M., 1969, INORG CHIM ACTA, V3, P227

[2] Biomimetic synthesis of biatractylolide and biepiasterolide [J].

Bagal, SK ;

Adlington, RM ;

Baldwin, JE ;

Marquez, R ;

Cowley, A .

ORGANIC LETTERS, 2003, 5 (17) :3049-3052

[3] Studies towards the biomimetic synthesis of bisesquiterpene lactones [J].

Bagal, SK ;

Adlington, RM ;

Marquez, R ;

Cowley, AR ;

Baldwin, JE .

TETRAHEDRON LETTERS, 2003, 44 (27) :4993-4996

[4] CAPTODATIVE SUBSTITUENT EFFECTS .22. RADICAL DEHYDRODIMERISATION AND BRIDGED DEHYDRODIMERISATION OF MACROCYCLIC POLYETHERS [J].

BEAUJEAN, M ;

MIGNANI, S ;

MERENYI, R ;

JANOUSEK, Z ;

VIEHE, HG ;

KIRCH, M ;

LEHN, JM .

TETRAHEDRON, 1984, 40 (21) :4395-4400

[5] NATURALLY-OCCURRING TERPENE DERIVATIVES .241. NEW SESQUITERPENE LACTONE FROM ASTER-UMBELLATUS [J].

BOHLMANN, F ;

DUTTA, LN ;

KNAUF, W ;

ROBINSON, H ;

KING, RM .

PHYTOCHEMISTRY, 1980, 19 (03) :433-436

[6] FURANOLATE-BASED STRATEGY FOR SEQUENTIAL 2,3,4-TRISUBSTITUTION OF BUTENOLIDE - TOTAL SYNTHESIS OF NOSTOCLIDE-I AND NOSTOCLIDE-II [J].

BOUKOUVALAS, J ;

MALTAIS, F ;

LACHANCE, N .

TETRAHEDRON LETTERS, 1994, 35 (43) :7897-7900

[7] THE ACETYLENES FROM ATRACTYLODES-MACROCEPHALA [J].

CHEN, ZL .

PLANTA MEDICA, 1987, (05) :493-494

[8]

HIKINO H, 1962, CHEM PHARM BULL, V10, P641

[9]

HIKINO H, 1964, CHEM PHARM BULL, V12, P755

[10]

Huang Bao-Shan, 1992, Acta Botanica Sinica, V34, P614

← 1 2 3 4 →