The synthesis of 1,8-dihydroxynaphthalene-derived natural products:: palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin A and novel analogues

被引:52
作者
Ragot, JP [1 ]
Steeneck, C [1 ]
Alcaraz, ML [1 ]
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 08期
关键词
D O I
10.1039/a901076i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total syntheses of the title fungal metabolites are described via a route which utilises initial acetalisation with 1,8-dihydroxynaphthalene followed by elaboration of the ring A functionality. Novel analogues are also reported. Structural clarification is provided for palmarumycin C-11, bipendensin and Sch 53,823.
引用
收藏
页码:1073 / 1082
页数:10
相关论文
共 39 条
[1]   Manumycin A: Synthesis of the (+)-enantiomer and revision of stereochemical assignment [J].
Alcaraz, L ;
Macdonald, G ;
Ragot, JP ;
Lewis, N ;
Taylor, RJK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3526-3527
[2]  
ALCARAZ ML, UNPUB
[3]   Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371:: novel spiro-ketal fungal metabolites [J].
Barrett, AGM ;
Hamprecht, D ;
Meyer, T .
CHEMICAL COMMUNICATIONS, 1998, (07) :809-810
[4]   OXIDATION OF BENZYLIC HYDROCARBONS WITH BENZENESELENINIC ANHYDRIDE AND RELATED REACTIONS [J].
BARTON, DHR ;
HUI, RAHF ;
LEY, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2179-2185
[5]   DEHYDROGENATION OF STEROIDAL AND TRITERPENOID KETONES USING BENZENESELENINIC ANHYDRIDE [J].
BARTON, DHR ;
LESTER, DJ ;
LEY, SV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2209-2212
[6]   FACILE CONVERSION OF ELECTRON RICH BENZYLIC HYDROCARBONS TO CARBONYL-COMPOUNDS BY PEROXYDISULFATE AND COPPER IONS [J].
BHATT, MV ;
PERUMAL, PT .
TETRAHEDRON LETTERS, 1981, 22 (27) :2605-2608
[7]   Quantumchemical calculation of CD spectra: The absolute configuration of palmarumycins CP3 and C-2 [J].
Bringmann, G ;
Busemann, S ;
Krohn, K ;
Beckmann, K .
TETRAHEDRON, 1997, 53 (05) :1655-1664
[8]   TERT-BUTYL HYDROPEROXIDE PYRIDINIUM DICHROMATE - A CONVENIENT REAGENT SYSTEM FOR ALLYLIC AND BENZYLIC OXIDATIONS [J].
CHIDAMBARAM, N ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :5048-5051
[9]   STRUCTURE OF SCH-49209 - A NOVEL ANTITUMOR AGENT FROM THE FUNGUS NATTRASSIA-MANGIFERAE [J].
CHU, M ;
TRUUMEES, I ;
PATEL, MG ;
GULLO, VP ;
PUAR, MS ;
MCPHAIL, AT .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :1222-1223
[10]   SCH 53823 and SCH 53825, novel fungal metabolites with phospholipase D inhibitory activity [J].
Chu, M ;
Patel, MG ;
Pai, JK ;
Das, PR ;
Puar, MS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (05) :579-584