TOTAL SYNTHESIS OF RACEMIC GEIJERONE AND GAMMA-ELEMENE

被引：8

作者：

KATO, M ^{[1
]}

KURIHARA, H ^{[1
]}

YOSHIKOSHI, A ^{[1
]}

机构：

[1] TOHOKU UNIV,NONAQUEOUS SOLUT CHEM RES INST,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 11期

关键词：

D O I：

10.1039/p19790002740

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Representative elemanoids, geijerone (4) and γ-elemene (5), were synthesised in racemic form via reductive fragmentation of 4β- methylsulphonyloxy-4,4a,5,6,8,8aα-hexahydro-1α,4aβ- dimethylnaphthalene-2,7(1H,3H)-dione 7-ethylene acetal (10) or 2β-hydroxy-4β-methylsulphonyloxy-2,3,4,4a,5,6,8,8aα-octahydro- 1α,4aβ-dimethylnaphthalen-7(1H)-one ethylene acetal (11), both readily available from the Wieland-Miescher ketone (3).

引用

页码：2740 / 2743

页数：4

共 10 条

[1]

BERNARDI R, 1970, CHIM IND-MILAN, V52, P581

[2]

GAUTEER C, 1971, HELV CHIM ACTA, V54, P183

[3] TERPENOID CHEMISTRY .8. STRUCTURE OF DELTA-ELEMENE [J].

GOUGH, JH ;

SUTHERLAND, MD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (11) :1270-&

[4] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS [J].

GROB, CA ;

SCHIESS, PW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :1-&

[5] STEREOSELECTIVE TOTAL SYNTHESIS OF GUAIAZULENIC SESQUITERPENOIDS ALPHA-BULNESENE AND BULNESOL [J].

HEATHCOC.CH ;

RATCLIFF.R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1746-&

[6] SYNTHESIS OF 4,4A-5,6,7,8-HEXAHYDRO-5BETA-HYDROXY-4ABETA,8ALPHA-DIMETHYLNAPHTHALEN-2(3H)-ONE, A VERSATILE INTERMEDIATE FOR SESQUITERPENE SYNTHESIS [J].

KATO, M ;

KURIHARA, H ;

KOSUGI, H ;

WATANABE, M ;

ASUKA, S ;

YOSHIKOSHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (22) :2433-2436

[7] SELECTIVE DEGRADATION OF GUAIOL - SYNTHESIS OF 7-EPIGUAIOL [J].

MARSHALL, JA ;

RUDEN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (17) :2569-&

[8]

MARSHALL JA, 1971, J ORG CHEM, V36, P2563

[9]

POSNER GH, 1975, TETRAHEDRON LETT, P1373

[10] GEIJERONE (3-ISOPROPENYL-4-METHYL-4-VINYLCYCLOHEXANONE) - NEW, NATURALLY OCCURRING C-12 TERPENOID [J].

THOMAS, AF .

HELVETICA CHIMICA ACTA, 1972, 55 (07) :2429-&

← 1 →