A catalytic asymmetric synthesis of a versatile intermediate for phorbol derivatives

被引:17
作者
Sato, H [1 ]
Kim, YS [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
cyclopropanation; asymmetric addition; nitrile oxide cycloaddition;
D O I
10.1016/S0040-4039(99)00340-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalytic asymmetric cyclopropanation of enol silyl ether 9 gave the lactone 3 in up to 78% ee. The lactone 3 was then transformed into 2, potentially a very versatile intermediate for phorbol analogs, using an intramolecular nitrile oxide cycloaddition as a key step. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2973 / 2976
页数:4
相关论文
共 20 条
[1]   AN IMPROVED METHOD FOR THE SYNTHESIS OF ALPHA-DIAZO KETONES [J].
DANHEISER, RL ;
MILLER, RF ;
BRISBOIS, RG ;
PARK, SZ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1959-1964
[2]   A CONVERGENT APPROACH TOWARD THE TIGLIANE RING-SYSTEM [J].
DAUBEN, WG ;
DINGES, J ;
SMITH, TC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7635-7637
[3]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[4]   ENANTIOCONTROL AND REGIOCONTROL IN LACTAM SYNTHESES BY INTRAMOLECULAR CARBON-HYDROGEN INSERTION REACTIONS OF DIAZOACETAMIDES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES [J].
DOYLE, MP ;
PROTOPOPOVA, MN ;
WINCHESTER, WR ;
DANIEL, KL .
TETRAHEDRON LETTERS, 1992, 33 (51) :7819-7822
[5]   DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP ;
WINCHESTER, WR ;
HOORN, JAA ;
LYNCH, V ;
SIMONSEN, SH ;
GHOSH, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978
[6]   ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS OF ALLYLIC AND HOMOALLYLIC DIAZOACETATES AND DIAZOACETAMIDES USING CHIRAL DIRHODIUM(II) CARBOXAMIDE CATALYSTS [J].
DOYLE, MP ;
AUSTIN, RE ;
BAILEY, AS ;
DWYER, MP ;
DYATKIN, AB ;
KALININ, AV ;
KWAN, MMY ;
LIRAS, S ;
OALMANN, CJ ;
PIETERS, RJ ;
PROTOPOPOVA, MN ;
RAAB, CE ;
ROOS, GHP ;
ZHOU, QL ;
MARTIN, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5763-5775
[7]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[8]   ENHANCEMENT OF ENANTIOSELECTIVITY IN INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXYLATES [J].
HASHIMOTO, S ;
WATANABE, N ;
SATO, T ;
SHIRO, M ;
IKEGAMI, S .
TETRAHEDRON LETTERS, 1993, 34 (32) :5109-5112
[9]   AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES [J].
LEVIN, JI ;
TUROS, E ;
WEINREB, SM .
SYNTHETIC COMMUNICATIONS, 1982, 12 (13) :989-993
[10]   THE ROLE OF PROTEIN KINASE-C IN CELL-SURFACE SIGNAL TRANSDUCTION AND TUMOR PROMOTION [J].
NISHIZUKA, Y .
NATURE, 1984, 308 (5961) :693-698