First total synthesis of (+)-chrysanthemol

被引：12

作者：

Chen, YG

Xiong, ZM

Zhou, G

Yang, J

Li, YL ^{[1
]}

机构：

[1] Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Inst Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY LETTERS | 1997年 / 12期

关键词：

D O I：

10.1246/cl.1997.1289

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of (+)-chrysanthemol (1) has been described starting from (+)-dihydrocarvone (4). The features of our synthesis are the high yield introduction of C-3-C-4 double bond into eudesmane skeleton and rearrangement of epoxide to allylic alcohol promoted by BF3 . OEt2-Bu4NI reagent. In our synthesis, (+)-alpha-eudesmol (5) has been used as a key intermediate.

引用

收藏

页码：1289 / 1290

页数：2

相关论文

共 23 条

[1]

BARTON DHR, 1953, CHEM CARBON COMPOU B, V2, P664

[2] ACID-CATALYZED REACTIONS OF 7,8-EPOXYISOPIMAR-15-ENES [J].

BLUNT, JW ;

BOYD, GS ;

HARTSHORN, MP ;

MUNRO, MHG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (05) :987-993

[3]

BOSE AK, 1973, TETRAHEDRON LETT, V40, P3937

[4] A NEW ROUTE FOR THE CONVERSION OF CARVONE INTO EUDESMANE SESQUITERPENES [J].

CAINE, D ;

STANHOPE, B .

TETRAHEDRON, 1987, 43 (23) :5545-5555

[5] SESQUITERPENE ACIDS FROM DITTRICHIA-VISCOSA [J].

CECCHERELLI, P ;

CURINI, M ;

MARCOTULLIO, MC ;

MENGHINI, A .

PHYTOCHEMISTRY, 1985, 24 (12) :2987-2989

[6] STUDIES IN SESQUITERPENES .25. A SYNTHESIS OF ALPHA-SELINENE [J].

CHETTY, GL ;

RAO, SK ;

DEV, S ;

BANERJEE, DK .

TETRAHEDRON, 1966, 22 (07) :2311-&

[7] TOTAL SYNTHESIS OF RACEMIC SELINA-3,7(11)-DIENE, ALPHA-SELINENE, AND ALPHA-EUDESMOL [J].

CHOU, TS ;

LEE, SJ ;

YAO, NK .

TETRAHEDRON, 1989, 45 (13) :4113-4124

[8] TOTAL SYNTHESIS OF DIHYDROCOSTUNOLIDE [J].

COREY, EJ ;

HORTMANN, AG .

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

[9] SESQUITERPENE XYLOSIDES FROM IPHIONA-SCABRA [J].

ELGHAZOULY, MG ;

ELSEBAKHY, NA ;

ELDIN, AAS ;

ZDERO, C ;

BOHLMANN, F .

PHYTOCHEMISTRY, 1987, 26 (02) :439-443

[10] BORON TRIFLUORIDE CATALYSED REARRANGEMENT OF 1,2-EPOXY LUPAN-3-1 [J].

GANGULY, AK ;

GOVINDAC.TR ;

MANMADE, A .

TETRAHEDRON, 1967, 23 (09) :3847-&