ENANTIOSELECTIVE SYNTHESIS OF (+)-DE-ISOPROPENYL NOOTKATONE

被引:6
作者
DAHURON, N [1 ]
LANGLOIS, N [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0957-4166(00)80430-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The absolute configuration of the delta-oxo acid 11, obtained through an asymmetric Michael-type reaction involving the activated chiral alpha,beta-unsaturated oxazoline 7, was established by comparison of the CD curves of the derived (+)-octalone 14 and (+)-nootkatone 15.
引用
收藏
页码:1901 / 1908
页数:8
相关论文
共 22 条
[1]   STUDIES IN STEROID TOTAL SYNTHESIS .4. A STEREOSELECTIVE RING A SYNTHESIS [J].
BARKLEY, LB ;
KNOWLES, WS ;
RAFFELSON, H ;
THOMPSON, QE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :4111-4116
[2]   A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].
CAZEAU, P ;
DUBOUDIN, F ;
MOULINES, F ;
BABOT, O ;
DUNOGUES, J .
TETRAHEDRON, 1987, 43 (09) :2075-2088
[3]  
CRABBE P, 1968, APPLICATIONS DISPERS, P443
[4]   THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES [J].
DANGELO, J ;
DESMAELE, D ;
DUMAS, F ;
GUINGANT, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :459-505
[5]  
DANIEL A, 1971, B SOC CHIM FR, P1060
[6]   FURTHER INVESTIGATION OF GRAPEFRUIT JUICE FLAVOR COMPONENTS (CITRUS-PARADISI MACFAYDEN) - VALENCANE-TYPE AND EUDESMANE-TYPE SESQUITERPENE KETONES [J].
DEMOLE, E ;
ENGGIST, P .
HELVETICA CHIMICA ACTA, 1983, 66 (05) :1381-1391
[7]   LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE [J].
DUHAMEL, P ;
DUJARDIN, G ;
HENNEQUIN, L ;
POIRIER, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :387-396
[8]  
GAWLEY RE, 1976, SYNTHESIS-STUTTGART, P777
[9]   STEROIDS .9. AN IMPROVED METHOD OF PREPARATION OF CHOLESTENONE-4-C-14 [J].
HEARD, RDH ;
ZIEGLER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (08) :4036-4038
[10]   CONFORMATION OF NOOTKATONE [J].
ISHIDA, T ;
MATSUURA, T .
EXPERIENTIA, 1970, 26 (09) :934-&