TOTAL SYNTHESIS OF DISCORHABDIN-C - A GENERAL AZA SPIRO DIENONE FORMATION FROM O-SILYLATED PHENOL DERIVATIVES USING A HYPERVALENT IODINE REAGENT

被引:187
作者
KITA, Y
TOHMA, H
INAGAKI, M
HATANAKA, K
YAKURA, T
机构
[1] Faculty of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565
关键词
D O I
10.1021/ja00032a036
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, which was isolated from the sponge of Latrunculia du Bocage in New Zealand, was achieved.
引用
收藏
页码:2175 / 2180
页数:6
相关论文
共 42 条
[1]  
ALVAREZ M, 1991, HETEROCYCLES, V32, P759
[2]   PREPARATION OF QUINONE-IMIDE KETALS FROM AMIDES WITH HYPERVALENT ORGANO-IODINE COMPOUNDS [J].
BARRET, R ;
DAUDON, M .
TETRAHEDRON LETTERS, 1991, 32 (19) :2133-2134
[3]   REVERSE PHASE FLASH CHROMATOGRAPHY - A METHOD FOR THE RAPID PARTITIONING OF NATURAL PRODUCT EXTRACTS [J].
BLUNT, JW ;
CALDER, VL ;
FENWICK, GD ;
LAKE, RJ ;
MCCOMBS, JD ;
MUNRO, MHG ;
PERRY, NB .
JOURNAL OF NATURAL PRODUCTS, 1987, 50 (02) :290-292
[4]   SYNTHETICALLY AND BIOLOGICALLY INTERESTING N-ACYLQUINONE IMINE KETALS AND N-ACYLQUINOL IMINE ETHERS FROM ANODIC-OXIDATION OF ANILIDES [J].
CHEN, CP ;
CHOU, CT ;
SWENTON, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :946-948
[5]   PRIANOSIN-B, PRIANOSIN-C, AND PRIANOSIN-D NOVEL SULFUR-CONTAINING ALKALOIDS WITH POTENT ANTINEOPLASTIC ACTIVITY FROM THE OKINAWAN MARINE SPONGE PRIANOS-MELANOS [J].
CHENG, JF ;
OHIZUMI, Y ;
WALCHLI, MR ;
NAKAMURA, H ;
HIRATA, Y ;
SASAKI, T ;
KOBAYASHI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4621-4624
[6]   SYNTHETIC STUDIES ON NOVEL SULFUR-CONTAINING ALKALOIDS, PRIANOSINS ISOLATED FROM THE MARINE SPONGE PRIANOS-MELANOS - SYNTHESIS OF THE SPIRODIENONE MOIETY BY PHENOLIC OXIDATION [J].
CHENG, JF ;
NISHIYAMA, S ;
YAMAMURA, S .
CHEMISTRY LETTERS, 1990, (09) :1591-1594
[7]   1,2-ADDITION OF SULFUR NUCLEOPHILES TO THE N-ACYLATED IMINE LINKAGE - A MODEL STUDY FOR THE INCORPORATION OF SULFUR NUCLEOPHILES DURING METABOLISM OF ACYLATED AROMATIC-AMINES [J].
CLARK, WM ;
SWENTON, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :3969-3971
[8]   THE USE OF HETEROCYCLIC CHEMISTRY IN THE SYNTHESIS OF NATURAL AND UNNATURAL PRODUCTS [J].
CONFALONE, PN .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (01) :31-46
[10]  
HAMABUCHI S, 1991, HETEROCYCLES, V32, P443