A catalytic enantioselective approach to chromans and chromanols. A total synthesis of (-)-calanolides A and B and the vitamin E nucleus

被引:190
作者
Trost, BM [1 ]
Toste, FD [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja981142k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:9074 / 9075
页数:2
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共 34 条
[1]   Experiments on the synthesis of rotenone and its derivatives. Part XII. The 2 : 2-dimethyl-Delta(3)-chromen residue of toxicarol. [J].
Bridge, W ;
Heyes, RG ;
Robertson, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1937, :279-285
[2]  
CLARK WC, 1983, J AM CHEM SOC, V105, P2487
[3]   ENANTIOSELECTIVE CARBON-DIOXIDE EXTRUSION FROM ALLYL PHENYL CARBONATES BY NICKEL, PALLADIUM AND RHODIUM CATALYSTS [J].
CONSIGLIO, G ;
SCALONE, M ;
RAMA, F .
JOURNAL OF MOLECULAR CATALYSIS, 1989, 50 (02) :L11-L15
[4]   SYNTHESIS OF OPTICALLY-ACTIVE CALANOLIDE-A AND CALANOLIDE-B [J].
DESHPANDE, PP ;
TAGLIAFERRI, F ;
VICTORY, SF ;
YAN, SJ ;
BAKER, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2964-2965
[5]   RHODIUM(I)-CATALYZED AND IRIDIUM(I)-CATALYZED HYDROBORATION REACTIONS - SCOPE AND SYNTHETIC APPLICATIONS [J].
EVANS, DA ;
FU, GC ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6671-6679
[6]   HIV-inhibitory natural products .30. Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B [J].
Galinis, DL ;
Fuller, RW ;
McKee, TC ;
Cardellina, JH ;
Gulakowski, RJ ;
McMahon, JB ;
Boyd, MR .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (22) :4507-4510
[7]   STEREOSELECTIVITY AND REGIOSELECTIVITY IN PALLADIUM-CATALYZED ALLYLIC ETHERIFICATION [J].
GOUX, C ;
MASSACRET, M ;
LHOSTE, P ;
SINOU, D .
ORGANOMETALLICS, 1995, 14 (10) :4585-4593
[8]  
GOUX C, 1992, SYNLETT, P725
[9]  
HAMAMURA K, Patent No. 01233278
[10]   ENANTIOSELECTIVE FUNCTIONALIZATION OF PROCHIRAL DIOLS VIA CHIRAL SPIROKETALS - PREPARATION OF OPTICALLY PURE 2-SUBSTITUTED 1,3-PROPANEDIOL DERIVATIVES AND ASYMMETRIC-SYNTHESIS OF CHROMAN RING AND SIDE-CHAIN OF ALPHA-TOCOPHEROL [J].
HARADA, T ;
HAYASHIYA, T ;
WADA, I ;
IWAAKE, N ;
OKU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :527-532