ORTHO-VANILLYL ALCOHOL AS A SYNTHETIC EQUIVALENT OF 2-METHOXYCYCLOHEXA-2,4-DIENONES - A NOVEL SYNTHESIS OF LINEARLY FUSED CIS-ANTI-CIS-TRICYCLOPENTANOIDS

被引:34
作者
SINGH, V
THOMAS, B
机构
关键词
D O I
10.1039/c39920001211
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and efficient synthesis of tricyclopentanoids via inverse demand pi-4s + pi-2s cycloaddition and photochemical reaction of annulated[2.2.2]octenones having an alpha-alkoxy-beta,gamma-unsaturated carbonyl chromophore, is described.
引用
收藏
页码:1211 / 1213
页数:3
相关论文
共 30 条
[1]   PERIODATE OXIDATION OF PHENOLS .9. OXIDATION OF ORTHO (OMEGA-HYDROXYALKYL) PHENOLS [J].
ADLER, E ;
BRASEN, S ;
MIYAKE, H .
ACTA CHEMICA SCANDINAVICA, 1971, 25 (06) :2055-&
[2]  
Aldridge DC, 1983, FUNGAL METABOLITES, V2
[3]  
AYER WA, 1981, TETRAHEDRON, V37, P2199, DOI 10.1016/S0040-4020(01)97979-7
[4]   CAPNELLANE SESQUITERPENES - TOTAL SYNTHESIS OF EPIPRECAPNELLADIENE AND DELTA-8(9)-CAPNELLENE [J].
BIRCH, AM ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1913-1917
[5]   STRUCTURE AND CHEMISTRY OF HIRSUTIC ACID [J].
COMER, FW ;
MCCAPRA, F ;
QURESHI, IH ;
SCOTT, AI .
TETRAHEDRON, 1967, 23 (12) :4761-&
[6]   RADICAL TRANSLOCATION REACTIONS OF ORTHO-IODOANILIDES - THE USE OF CARBON HYDROGEN-BONDS AS PRECURSORS OF RADICALS ADJACENT TO CARBONYL GROUPS [J].
CURRAN, DP ;
ABRAHAM, AC ;
LIU, HT .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4335-4337
[7]   SUBSTITUENT AND STRUCTURAL EFFECTS ON THE PHOTOCHEMISTRY OF BICYCLIC BETA-GAMMA-UNSATURATED KETONES [J].
ECKERSLEY, TJ ;
PARKER, SD ;
ROGERS, NAJ .
TETRAHEDRON, 1984, 40 (19) :3749-3758
[8]   SESQUITERPENE ALCOHOLS WITH NOVEL SKELETONS FROM THE FUNGUS CERATOCYSTIS-PICEAE (ASCOMYCOTINA) [J].
HANSSEN, HP ;
ABRAHAM, WR .
TETRAHEDRON, 1988, 44 (08) :2175-2180
[9]  
HIJFTE L. V., 1987, J ORG CHEM, V2, P4647
[10]   PHOTOCHEMISTRY AND SPECTROSCOPY OF BETA, GAMMA-UNSATURATED CARBONYL-COMPOUNDS [J].
HOUK, KN .
CHEMICAL REVIEWS, 1976, 76 (01) :1-74