ANTI-AIDS AGENTS .22. ASYMMETRIC-SYNTHESIS OF 3',4'-DI-O-(-)-CAMPHANOYL-(+)-CIS-KHELLACTONE (DCK), A POTENT ANTI-HIV AGENT

被引:23
作者
XIE, L
CRIMMINS, MT
LEE, KH
机构
[1] UNIV N CAROLINA,SCH PHARM,DIV MED CHEM & NAT PROD,NAT PROD LAB,CHAPEL HILL,NC 27599
[2] UNIV N CAROLINA,DEPT CHEM,VENABLE & KENAN LABS CHEM,CHAPEL HILL,NC 27599
关键词
D O I
10.1016/0040-4039(95)00862-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient asymmetric synthesis of 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (DCK) (1) via catalytic asymmetric dihydroxylation is reported. Among seven commercial ligands investigated, (DHQ)(2)-PYR is the mast enantioselective ligand for the catalytic asymmetric dihydroxylation of seselin (5), a synthetic intermediate of DCK, and affords up to 86% e.e.
引用
收藏
页码:4529 / 4532
页数:4
相关论文
共 12 条
[1]   SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].
AMBERG, W ;
BENNANI, YL ;
CHADHA, RK ;
CRISPINO, GA ;
DAVIS, WD ;
HARTUNG, J ;
JEONG, KS ;
OGINO, Y ;
SHIBATA, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :844-849
[2]   ASYMMETRIC DIHYDROXYLATION OF SQUALENE [J].
CRISPINO, GA ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1992, 33 (30) :4273-4274
[3]   IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].
CRISPINO, GA ;
JEONG, KS ;
KOLB, HC ;
WANG, ZM ;
XU, DQ ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786
[4]  
HLUBUEK J, 1971, AUST J CHEM, V62, P2347
[5]   ANTI-AIDS AGENTS .14. 3',4'-DI-O-(-)-CAMPHANOYL-(+)-CIS-KHELLACTONE AND RELATED-COMPOUNDS - A NEW CLASS OF POTENT ANTI-HIV AGENTS [J].
HUANG, L ;
KASHIWADA, Y ;
COSENTINO, LM ;
FAN, S ;
LEE, KH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (04) :593-598
[6]   ANTI-AIDS AGENTS .15. SYNTHESIS AND ANTI-HIV ACTIVITY OF DIHYDROSESELINS AND RELATED ANALOGS [J].
HUANG, L ;
KASHIWADA, Y ;
COSENTINO, LM ;
FAN, S ;
CHEN, CH ;
MCPHAIL, AT ;
FUJIOKA, T ;
MIHASHI, K ;
LEE, KH .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (23) :3947-3955
[7]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970
[8]  
KONOSHIMA T, IN PRESS J NAT PROD
[9]   NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].
SHARPLESS, KB ;
AMBERG, W ;
BELLER, M ;
CHEN, H ;
HARTUNG, J ;
KAWANAMI, Y ;
LUBBEN, D ;
MANOURY, E ;
OGINO, Y ;
SHIBATA, T ;
UKITA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4585-4588
[10]   THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].
SHARPLESS, KB ;
AMBERG, W ;
BENNANI, YL ;
CRISPINO, GA ;
HARTUNG, J ;
JEONG, KS ;
KWONG, HL ;
MORIKAWA, K ;
WANG, ZM ;
XU, DQ ;
ZHANG, XL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771