THE SYNTHESIS OF (+)-HEDYCARYOL, STARTING FROM NATURAL (-)-GUAIOL

被引：25

作者：

MINNAARD, AJ ^{[1
]}

WIJNBERG, JBPA ^{[1
]}

DEGROOT, A ^{[1
]}

机构：

[1] AGR UNIV WAGENINGEN, ORGAN CHEM LAB, 6703 HB WAGENINGEN, NETHERLANDS

来源：

TETRAHEDRON | 1994年 / 50卷 / 16期

关键词：

SESQUITERPENES; GERMACRANE; EUDESMANE; CADINANE; GAMMA-EUDESMOL;

D O I：

10.1016/S0040-4020(01)85014-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from the readily available (-)-guaiol the germacrane sesquiterpene (+)-hedycaryol can be synthesized in a 7 steps reaction sequence in an overall yield of 16%. Additionally, (+)-gamma-eudesmol has been synthesized, also starting from (-)-guaiol.

引用

页码：4755 / 4764

页数：10

共 27 条

[1]

BATES RB, 1962, CHEM IND-LONDON, P1759

[2] THE STRUCTURE OF THE DECALONE OBTAINED FROM THE OXIDATION OF GUAIOL [J].

CARMAN, RM ;

GARNER, AC ;

ROBINSON, WT .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (02) :327-335

[3]

COREY EJ, 1969, TETRAHEDRON LETT, P1779

[4] TERPENOIDS FROM THE SEED OF THUJOPSIS-DOLABRATA [J].

HASEGAWA, S ;

HIROSE, Y .

PHYTOCHEMISTRY, 1981, 20 (03) :508-510

[5] STEREOCHEMICAL IMPLICATIONS IN SESQUITERPENE BIOGENESIS [J].

HENDRICKSON, JB .

TETRAHEDRON, 1959, 7 (1-2) :82-89

[6]

ITOKAWA H, 1983, CHEM PHARM BULL, V31, P1991

[7] HEDYCARYOL PRECUSOR OF ELEMOL [J].

JONES, RVH ;

SUTHERLA.MD .

CHEMICAL COMMUNICATIONS, 1968, (20) :1229-&

[8]

JONES RVH, 1970, TETRAHEDRON, P892

[9]

KITAGAWA I, 1974, CHEM PHARM BULL, V22, P2662

[10]

KODAMA M, 1979, TETRAHEDRON LETT, P1687

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