Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione

被引：59

作者：

Donkervoort, JG ^{[1
]}

Gordon, AR ^{[1
]}

Johnstone, C ^{[1
]}

Kerr, WJ ^{[1
]}

Lange, U ^{[1
]}

机构：

[1] UNIV STRATHCLYDE,DEPT PURE & APPL CHEM,GLASGOW G1 1XL,LANARK,SCOTLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 21期

关键词：

D O I：

10.1016/0040-4020(96)00259-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two complementary Pauson-Khand annulation protocols for use with the gaseous alkene, ethylene, are described These N-oxide promoted reactions (10 examples) are shown to proceed under both mild autoclave conditions or, more conveniently, at atmospheric pressure. The developed methodology has been utilised as the key transformation in the total synthesis of the sesquiterpene (+)-taylorione which has been realised in a good overall yield from readily available (+)-2-carene. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7391 / 7420

页数：30

共 119 条

[11]

Billington D. C., 1988, J CHEM RES M, P2601

[12] A SYNTHESIS OF JAPANESE HOP ETHER [J].

BILLINGTON, DC ;

KERR, WJ ;

PAUSON, PL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 328 (1-2) :223-227

[13] METHYLENOMYCIN-B - AN EFFICIENT SYNTHESIS FROM (2-BUTYNE)HEXACARBONYLDICOBALT [J].

BILLINGTON, DC ;

PAUSON, PL .

ORGANOMETALLICS, 1982, 1 (12) :1560-1561

[14] FORMATION AND REACTIVITY OF TRIMETHYLSILYLMETHYL CYCLOPENTENONES [J].

BILLINGTON, DC ;

KERR, WJ ;

PAUSON, PL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) :181-185

[15] THE EFFECT OF ULTRASOUND AND OF PHOSPHINE AND PHOSPHINE-OXIDES ON THE KHAND REACTION [J].

BILLINGTON, DC ;

HELPS, IM ;

PAUSON, PL ;

THOMSON, W ;

WILLISON, D .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 354 (02) :233-242

[16] A DIRECT ORGANOCOBALT MEDIATED SYNTHESIS OF SUBSTITUTED 3-OXABICYCLO[3.3.0]OCT-7-EN-6-ONES [J].

BILLINGTON, DC .

TETRAHEDRON LETTERS, 1983, 24 (28) :2905-2908

[17] STEROIDS .120. SYNTHESIS OF HALOGENATED STEROID HORMONES - NEW ROUTES TO 6-ALPHA-FLUOROTESTOSTERONE AND THE 6-ALPHA-FLUORO AND 6-BETA-FLUORO ANALOGS OF PROGESTERONE - THE SYNTHESIS OF 6-ALPHA-FLUORO AND 6-BETA-FLUORO REICHSTEINS COMPOUND-S AND 6-ALPHA-FLUORODESOXYCORTICOSTERONE AND 6-BETA-FLUORODESOXYCORTICOSTERONE ACETATE [J].

BOWERS, A ;

IBANEZ, LC ;

RINGOLD, HJ .

TETRAHEDRON, 1959, 7 (1-2) :138-152

[18] SELECTIVE REDUCTIONS .39. PARTIAL REDUCTION OF CARBOXYLIC-ACIDS WITH THEXYLCHLOROBORANE-METHYL SULFIDE - A DIRECT AND SIMPLE ALDEHYDE SYNTHESIS [J].

BROWN, HC ;

CHA, JS ;

YOON, NM ;

NAZER, B .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5400-5406

[19] DIRECT ENTRY TO THE ALL-CIS TRICYCLO[5.2.1.04,10]DECANE (PERHYDROTRIQUINACENE) SKELETON BY A COBALT MEDIATED INTRAMOLECULAR CYCLIZATION [J].

CARCELLER, E ;

CENTELLAS, V ;

MOYANO, A ;

PERICAS, MA ;

SERRATOSA, F .

TETRAHEDRON LETTERS, 1985, 26 (20) :2475-2476

[20] SYNTHESIS OF TRIQUINACENE DERIVATIVES - NEW APPROACH TOWARDS THE SYNTHESIS OF DODECAHEDRANE [J].

CARCELLER, E ;

GARCIA, ML ;

MOYANO, A ;

PERICAS, MA ;

SERRATOSA, F .

TETRAHEDRON, 1986, 42 (06) :1831-1839

← 1 2 3 4 5 6 7 8 9 10 →