Exploitation of chemical predisposition in synthesis: an approach to the manzamenones

被引:27
作者
Al-Busafi, S
Doncaster, JR
Drew, MGB
Regan, AC
Whitehead, RC
机构
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 04期
关键词
D O I
10.1039/b110829h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Full details of the syntheses of manzamenones A, C and F are reported, using an approach modelled on a plausible biogenetic theory. The key step of the approach is a "one-pot" conversion of the antileukemic cyclopentenone, untenone A, to manzamenone A which occurs in reasonable yield and which proceeds via a reaction sequence of dehydration, Diels-Alder dimerisation and retro-Dieckmann reaction. The synthetic approach has also been applied to the preparation of a number of shorter alkyl chain analogues of the natural products. Using a combination of NMR and X-ray crystallographic data for the shorter alkyl chain analogues of manzamenone A, it is suggested that the relative stereostructures of the majority of the manzamenones should be revised such that the acyl group at the C2 position lies on the alpha-face and that at the C5 position resides on the beta-face.
引用
收藏
页码:476 / 484
页数:9
相关论文
共 24 条
[1]   Pre-disposition in synthesis: An approach to the manzamenones [J].
Al-Busafi, S ;
Drew, MGB ;
Sanders, T ;
Whitehead, RC .
TETRAHEDRON LETTERS, 1998, 39 (12) :1647-1650
[2]   Predisposition in synthesis:: efficient routes to (±)-untenone A and (±)-manzamenones A, C and F [J].
Al-Busafi, S ;
Whitehead, RC .
TETRAHEDRON LETTERS, 2000, 41 (18) :3467-3470
[3]  
[Anonymous], 1993, PROGRAM CRYSTAL STRU
[4]   TRAPPING OF CYCLOPENTADIENONE AS A 4-PI COMPONENT IN DIELS-ALDER REACTIONS WITH ETHYL ACRYLATE - A SIMPLE SYNTHESIS OF (+/-)-SARKOMYCIN [J].
BARALDI, PG ;
BARCO, A ;
BENETTI, S ;
POLLINI, GP ;
POLO, E ;
SIMONI, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (16) :1049-1050
[5]   CYCLOPENTENONE SYNTHESIS BY DIRECTED CYCLIZATION [J].
FINCH, N ;
FITT, JJ ;
HSU, IHC .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (21) :3191-&
[6]  
GERWICK WH, 1993, TOP CURR CHEM, V167, P117
[7]  
HASHIMOTO N, 1981, CHEM PHARM BULL, V29, P1475
[8]   UNTENONE-A, A NEW CYCLOPENTENONE FROM THE OKINAWAN MARINE SPONGE PLAKORTIS SP CORRESPONDING TO THE DIENOPHILE IN THE BIOSYNTHESIS OF MANZAMENONES [J].
ISHIBASHI, M ;
TAKEUCHI, S ;
KOBAYASHI, J .
TETRAHEDRON LETTERS, 1993, 34 (23) :3749-3750
[10]   MANZAMENONES-G AND H, NEW DIMERIC FATTY-ACID DERIVATIVES FROM THE OKINAWAN MARINE SPONGE PLAKORTIS SP [J].
KOBAYASHI, J ;
TSUKAMOTO, S ;
TAKEUCHI, S ;
ISHIBASHI, M .
TETRAHEDRON, 1993, 49 (27) :5955-5960