A NEW ROUTE TO GAMMA-SUBSTITUTED GAMMA-LACTONES AND DELTA-SUBSTITUTED DELTA-LACTONES BASED ON THE REGIOSELECTIVE BETA-SCISSION OF ALKOXYL RADICALS GENERATED FROM TRANSANNULAR HEMIACETALS

被引:21
作者
KOBAYASHI, K [1 ]
SASAKI, A [1 ]
KANNO, Y [1 ]
SUGINOME, H [1 ]
机构
[1] HOKKAIDO UNIV,FAC ENGN,DIV ORGAN SYNTH,SAPPORO,HOKKAIDO 060,JAPAN
关键词
GAMMA-LACTONES; DELTA-LACTONES; MERCURY(II) OXIDE-IODINE REAGENT; PHOTOLYSIS; BETA-SCISSION OF ALKOXYL RADICALS;
D O I
10.1016/S0040-4020(01)89727-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new general synthesis of gamma-substituted gamma-lactones and delta-substituted delta-lactones including dihydro-5-octyl-2(3H)-furanone, a natural pheromone, is described. The synthesis involves the regioselective beta-scission of alkoxyl radicals generated from transannular hemiacetals as the key step.
引用
收藏
页码:7245 / 7258
页数:14
相关论文
共 33 条
[1]   GAMMA-SUBSTITUTED BUTYROLACTONES FROM ACROLEIN AND CARBONYL-COMPOUNDS [J].
BARLUENGA, J ;
FERNANDEZ, JR ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) :1534-1535
[2]   PHASE-TRANSFER CATALYSIS AND HOMOGENEOUS REACTIONS WITH BETA-OXYALKYL RADICALS FROM ORGANOMERCURIALS [J].
BARLUENGA, J ;
LOPEZPRADO, J ;
CAMPOS, PJ ;
ASENSIO, G .
TETRAHEDRON, 1983, 39 (17) :2863-2868
[3]  
BARUA NC, 1986, SYNTHESIS-STUTTGART, P1067
[4]   OXIDATION OF TETRAHYDROFURAN METHANOL DERIVATIVES WITH PYRIDINIUM CHLOROCHROMATE - A FACILE SYNTHESIS OF GAMMA-BUTYROLACTONES [J].
BASKARAN, S ;
CHANDRASEKARAN, S .
TETRAHEDRON LETTERS, 1990, 31 (19) :2775-2778
[5]   A GENERAL-APPROACH TO THE SYNTHESIS OF BUTANOLIDES - SYNTHESIS OF THE SEX-PHEROMONE OF THE JAPANESE BEETLE [J].
BASKARAN, S ;
ISLAM, I ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :891-895
[6]   SYNTHESIS OF GAMMA-LACTONES FROM ALKENES EMPLOYING PARA-METHOXYBENZYL CHLORIDE AS +CH2-CO2- EQUIVALENT [J].
BAUML, E ;
TSCHESCHLOK, K ;
POCK, R ;
MAYR, H .
TETRAHEDRON LETTERS, 1988, 29 (52) :6925-6926
[7]   PROXIMITY EFFECTS .8. SOLVOLYSIS OF CIS-CYCLOOCTENE OXIDE - SYNTHESIS OF ALCOHOLS IN THE CYCLOOCTANE SERIES [J].
COPE, AC ;
KEOUGH, AH ;
PETERSON, PE ;
SIMMONS, HE ;
WOOD, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3900-3905
[8]   PROXIMITY EFFECTS .10. CIS-1,4-CYCLOHEPTANEDIOL FROM SOLVOLYSIS OF CYCLOHEPTENE OXIDE [J].
COPE, AC ;
LISS, TA ;
WOOD, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (23) :6287-6292
[9]   SYNTHESIS OF BETA- AND GAMMA-PHENYLTROPOLONES FROM 1,4-CYCLOHEXANEDIONE [J].
DOERING, WE ;
SAYIGH, AAR .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1365-&
[10]   SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE [J].
FUKUZAWA, S ;
NAKANISHI, A ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1669-1675