DIENES AS CHIRAL TEMPLATES - EASY ACCESS TO PURE (2S,3S,4R)-4-HYDROXY-2,3-EPOXYCYCLOHEX-5-EN-1-ONE

被引:8
作者
MAUVAIS, A [1 ]
WINTERFELDT, E [1 ]
机构
[1] UNIV HANNOVER,INST ORGAN CHEM,SCHNEIDERBERG 1B,W-3000 HANNOVER 1,GERMANY
关键词
CHIRAL DIENE; CHIRAL TEMPLATE; RETRO-DIELS-ALDER REACTION; FLASH VACUUM THERMOLYSIS; FAVORSKII REARRANGEMENT;
D O I
10.1016/S0040-4020(01)87948-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound 6 was obtained stereospecifically through a concise sequence including a Diels-Alder reaction with the chiral diene 2 and the retro reaction. The Favorskii rearrangement starting from the intermediate epoxide 4 was found to be regioselective.
引用
收藏
页码:5817 / 5822
页数:6
相关论文
共 9 条
[1]   CYCLOPENTADIENES AS CHIRAL TEMPLATES .4. AN EASY ACCESS TO (S)-HYDROXYCYCLOHEXENONE AND (R)-HYDROXYCYCLOHEXENONE [J].
BRUNJES, R ;
TILSTAM, U ;
WINTERFELDT, E .
CHEMISCHE BERICHTE, 1991, 124 (07) :1677-1678
[2]   ORGANIC-REACTIONS AT HIGH-PRESSURE - THE DIELS-ALDER REACTION OF PARA-BENZOQUINONE WITH DIENIC ESTERS [J].
DAUBEN, WG ;
BAKER, WR .
TETRAHEDRON LETTERS, 1982, 23 (26) :2611-2614
[3]   4-ACETOXYCYCLOPENT-2-ENONE - A SYNTHETIC EQUIVALENT FOR CYCLOPENTADIENONE IN DIELS-ALDER REACTIONS [J].
DOLS, PPMA ;
LACROIX, L ;
KLUNDER, AJH ;
ZWANENBURG, B .
TETRAHEDRON LETTERS, 1991, 32 (30) :3739-3742
[4]   FACILE RETRO DIELS-ALDER REACTION OF A PENTAMETHYLTRICYCLO[5.2.1.0/2,6]DECENONE DERIVATIVE - SYNTHESIS OF (+)-15(S)-PROSTAGLANDIN-A2 [J].
GRIECO, PA ;
ABOOD, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :410-412
[5]   SODIUM PERBORATE - A MILD AND CONVENIENT REAGENT FOR EFFICIENTLY OXIDIZING TRIALKYLBORANES [J].
KABALKA, GW ;
SHOUP, TM ;
GOUDGAON, NM .
TETRAHEDRON LETTERS, 1989, 30 (12) :1483-1486
[6]  
MATCHEVA K, 1989, SYNTHESIS-STUTTGART, P814
[7]   ENANTIODIVERGENT ROUTE TO CONDURITOL-C VIA LIPASE-MEDIATED ASYMMETRIZATION [J].
TAKANO, S ;
MORIYA, M ;
HIGASHI, Y ;
OGASAWARA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :177-178
[8]   ENANTIOMERICALLY PURE CYCLOPENTADIENES [J].
WINTERFELDT, E .
CHEMICAL REVIEWS, 1993, 93 (02) :827-843
[9]   THE TOTAL SYNTHESIS OF RESERPINE [J].
WOODWARD, RB ;
BADER, FE ;
BICKEL, H ;
FREY, AJ ;
KIERSTEAD, RW .
TETRAHEDRON, 1958, 2 (1-2) :1-57