Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4+2] benzannulation:: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2

被引:117
作者
Sato, K [1 ]
Asao, N [1 ]
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/jo051444m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B-2, is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone natural products, by using gold-catalyzed intramolecular [4 + 2] benzannulation reaction.
引用
收藏
页码:8977 / 8981
页数:5
相关论文
共 36 条
[1]   PYRIDINIUM YLIDES IN SYNTHESES OF NAPHTHOPYRANDIONES AND IN REGIOSELECTIVE SYNTHESES OF ACYLATED ANTHRAQUINONES RELATED TO FUNGAL AND BACTERIAL METABOLITES [J].
ALDERSLEY, MF ;
CHISHTI, SH ;
DEAN, FM ;
DOUGLAS, ME ;
ENNIS, DS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2163-2174
[2]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[3]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[4]   AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].
Asao, N ;
Sato, K ;
Menggenbateer ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685
[5]  
BOWIE J. H., 1967, TETRAHEDRON LETT, V16, P1449
[6]   Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols [J].
Buffet, MF ;
Dixon, DJ ;
Ley, SV ;
Reynolds, DJ ;
Storer, RI .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (08) :1145-1154
[7]   SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes [J].
Bull, SD ;
Davies, SG ;
Nicholson, RL ;
Sanganee, HJ ;
Smith, AD .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (16) :2886-2899
[8]  
Carreño MC, 1999, CHEM COMMUN, P817
[9]   Total synthesis of heliophenanthrone [J].
Dyker, G ;
Hildebrandt, D .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :6093-6096
[10]  
GOUND SJ, 1994, J AM CHEM SOC, V116, P1800