POLYFUNCTIONAL BICYCLO[6.3.0]UNDECANE INTERMEDIATES

被引：7

作者：

CHORLTON, AP ^{[1
]}

MORRIS, GA ^{[1
]}

SUTHERLAND, JK ^{[1
]}

机构：

[1] VICTORIA UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 05期

关键词：

D O I：

10.1039/p19910001205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On thermolysis, 2-hydroxy-1-isopropyl-2-vinylbicyclo[4.3.0]non-6-en-8-one 18 undergoes oxy-Cope rearrangement followed by an 'ene' reaction to give 5-hydroxy-11-isopropyl-8-methyltricyclo[6.3.0.0(1,5)]undec-10-ene-9-one 21, which is cleaved by Pb(OAc)4-I2 to 11-isopropyl-8-methylbicyclo[6.3.0]undeca-1,10-diene-5,9-dione 23. Aspects of the chemistry of the dione are explored.

引用

页码：1205 / 1210

页数：6

共 14 条

[1]

BOENIGK W, 1984, THESIS U DUSSELDORF

[2]

DAUBEN WG, 1977, J ORG CHEM, V42, P3787, DOI 10.1021/jo00444a001

[3] [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT [J].

EVANS, DA ;

GOLOB, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4765-4766

[4]

MYSTRE C, 1962, HELV CHIM ACTA, V45, P1317

[5]

OHTA M, 1968, J ORG CHEM, V33, P3504

[6]

PAQUETTE LA, 1983, J ORG CHEM, V48, P1148

[7]

PATTENDEN G, 1983, J CHEM SOC P1, P1913

[8] ALKYLATION OF 1,5-DIMETHOXY-1,4-CYCLOHEXADIENE - CONVENIENT SYNTHESIS OF 2-ALKYL-1,3-CYCLOHEXANEDIONE AND 2-ALKENYL-1,3-CYCLOHEXANEDIONE [J].

PIERS, E ;

GRIERSON, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3755-3757

[9] LEWIS ACID MEDIATED VERSION OF THE NICHOLAS REACTION - SYNTHESIS OF SYN-ALKYLATED PRODUCTS AND COBALT-COMPLEXED CYCLOALKYNES [J].

SCHREIBER, SL ;

SAMMAKIA, T ;

CROWE, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3128-3130

[10]

SWAMINATHAN S, 1962, TETRAHEDRON LETT, P729

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