A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)-5,7-O-DIMETHYLEUCOMOL AND (S)-5,7-O-DIMETHYLEUCOMOL

被引:28
作者
DAVIS, FA
CHEN, BC
机构
关键词
D O I
10.1016/S0040-4039(00)97181-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both (R)- and (S)-5,7-O-dimethyleucomol 1b (R = Me) were synthesized in 57% overall yield in >96% enantiomeric excess. The key step involves the enantioselective α hydroxylation of the lithium enolate of 8 by readily available (+)- and (-)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine 9c. © 1990.
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页码:6823 / 6826
页数:4
相关论文
共 22 条
[1]   ABSOLUTE-CONFIGURATION OF HOMOISOFLAVANONES FROM MUSCARI SPECIES [J].
ADINOLFI, M ;
BARONE, G ;
CORSARO, MM ;
MANGONI, L ;
LANZETTA, R ;
PARRILLI, M .
TETRAHEDRON, 1988, 44 (15) :4981-4988
[2]   HOMOISOFLAVANONES FROM MUSCARI-NEGLECTUM [J].
BARONE, G ;
CORSARO, MM ;
LANZETTA, R ;
PARRILLI, M .
PHYTOCHEMISTRY, 1988, 27 (03) :921-923
[3]  
BLASKO G, 1988, HETEROCYCLES, V27, P445
[4]  
BOHLER P, 1967, TETRAHEDRON LETT, P3479
[5]   CHROMANE .17. DIE SYNTHESE VON (+-)-HAMATOXYLIN [J].
DANN, O ;
HOFMANN, H .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1498-&
[6]  
DAVE K. G., 1960, JOUR SCI AND INDUST RES, V19, P470
[7]   ENANTIOSELECTIVE SYNTHESIS OF TERTIARY ALPHA-HYDROXY CARBONYL-COMPOUNDS USING ((8,8-DICHLOROCAMPHORYL)SULFONYL)OXAZIRIDINE [J].
DAVIS, FA ;
WEISMILLER, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3715-3717
[8]   CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE [J].
DAVIS, FA ;
SHEPPARD, AC ;
CHEN, BC ;
HAQUE, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6679-6690
[9]   APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS [J].
DAVIS, FA ;
SHEPPARD, AC .
TETRAHEDRON, 1989, 45 (18) :5703-5742
[10]  
FARKAS L, 1970, TETRAHEDRON, V26, P2787