Synthesis of the bisbenzannelated spiroketal core of the γ-rubromycins.: The use of a novel Nef-type reaction mediated by Pearlman's catalyst

被引:46
作者
Capecchi, T [1 ]
de Koning, CB [1 ]
Michael, JP [1 ]
机构
[1] Univ Witwatersrand, Dept Chem, Ctr Mol Design, ZA-2050 Witwatersrand, South Africa
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 16期
关键词
D O I
10.1039/b002984j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the bisbenzannelated spiroketal core 6 of the gamma-rubromycin 1 from the substituted nitrostyrene 20 was achieved by using a novel Nef-type reaction mediated by Pearlman's catalyst. The precursor 28 was synthesised from readily prepared starting materials using Henry condensation chemistry. The product 6 was found to exist in two conformations in solution as shown by NMR spectroscopy.
引用
收藏
页码:2681 / 2688
页数:8
相关论文
共 44 条
[1]   HYDROXY-FUNCTIONALIZED CONJUGATED NITROOLEFINS AS IMMEDIATE PRECURSORS OF SPIROKETALS - A NEW SYNTHESIS OF 1,7-DIOXASPIRO[5.5]UNDECANE AND (E)-2-METHYL-1,7-DIOXASPIRO[5.6]DODECANE [J].
BALLINI, R ;
PETRINI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (23) :3159-3160
[2]   NEW AND EFFICIENT SYNTHESIS OF OMEGA-NITROALCOHOLS AND SPIROKETALS BY CHEMIOSELECTIVE AND REGIOSELECTIVE REDUCTIVE CLEAVAGE OF 2-NITROCYCLOALKANONES [J].
BALLINI, R ;
PETRINI, M ;
ROSINI, G .
TETRAHEDRON, 1990, 46 (21) :7531-7538
[3]   Nitroaldol reaction in aqueous media: An important improvement of the Henry reaction [J].
Ballini, R ;
Bosica, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :425-427
[4]   STRUCTURE DETERMINATION OF PURPUROMYCIN, A NEW ANTIBIOTIC [J].
BARDONE, MR ;
MARTINELLI, E ;
ZERILLI, LF ;
CORONELLI, C .
TETRAHEDRON, 1974, 30 (16) :2747-2754
[6]   SYNTHESIS OF A PYRANONAPHTHOQUINONE-SPIROACETAL [J].
BRIMBLE, MA ;
NAIRN, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :579-583
[7]   A titanium naphtholate approach for the synthesis of analogues of griseusin A [J].
Brimble, MA ;
Nairn, MR ;
Park, JSO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :697-709
[8]   RUBROMYCINS .3. CONSTITUTION OF ALPHA-RUBROMYCIN, BETA-RUBROMYCIN, GAMMA-RUBROMYCIN, AND GAMMA-ISO-RUBROMYCIN [J].
BROCKMAN.H ;
ZEECK, A .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (06) :1709-&
[9]   Nitroalkenes as precursors to the aromatic spiroketal skeleton of γ-rubromycin.: A Nef-type reaction mediated by Pearlman's catalyst [J].
Capecchi, T ;
de Koning, CB ;
Michael, JP .
TETRAHEDRON LETTERS, 1998, 39 (30) :5429-5432
[10]  
CAPECCHI T, 1999, THESIS U WITWATERSRA