Total Synthesis of (+)-Clavilactone A and (-)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis

被引:45
作者
Takao, Ken-ichi [1 ]
Nanamiya, Ryuki [1 ]
Fukushima, Yuuki [1 ]
Namba, Ayumi [1 ]
Yoshida, Keisuke [1 ]
Tadano, Kin-ichi [1 ]
机构
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
REARRANGEMENT METATHESIS; STRUCTURE ELUCIDATION; MOSHER METHOD; ALDEHYDES; CLAVILACTONES; FACILE; BINOL; DIOLS; ACID;
D O I
10.1021/ol4027842
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective total synthesis of natural enantiomers of clavilactones A and B has been achieved. A key feature of the synthesis is the use of a ring-opening/ring-closing metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a gamma-butenolide.
引用
收藏
页码:5582 / 5585
页数:4
相关论文
共 32 条
[1]   SECONDARY MOLD METABOLITES .47. ISOLATION AND STRUCTURE ELUCIDATION OF CLAVILACTONES AC, NEW METABOLITES FROM THE FUNGUS CLITOCYBE CLAVIPES [J].
ARNONE, A ;
CARDILLO, R ;
MEILLE, SV ;
NASINI, G ;
TOLAZZI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2165-2168
[2]  
BLOCH R, 1991, SYNLETT, P829
[3]   THE SYNTHESIS OF CARYOPHYLLENIC ACID [J].
CAMPBELL, A ;
RYDON, HN .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (OCT) :3002-3008
[4]   Clavilactones, a novel class of tyrosine kinase inhibitors of fungal origin [J].
Cassinelli, G ;
Lanzi, C ;
Pensa, T ;
Gambetta, RA ;
Nasini, G ;
Cuccuru, G ;
Cassinis, M ;
Pratesi, G ;
Polizzi, D ;
Tortoreto, M ;
Zunino, F .
BIOCHEMICAL PHARMACOLOGY, 2000, 59 (12) :1539-1547
[5]   DIISOPROPYLSILYL DITRIFLATE AND DI-TERT-BUTYLSILYL DITRIFLATE - NEW REAGENTS FOR THE PROTECTION OF DIOLS [J].
COREY, EJ ;
HOPKINS, PB .
TETRAHEDRON LETTERS, 1982, 23 (47) :4871-4874
[6]   SOLVOLYSIS OF BICYCLO [2.1.0]PENTANE-1-METHYL P-NITROBENZOATE [J].
DAUBEN, WG ;
WISEMAN, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) :3545-&
[7]   ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].
FARINA, V ;
KAPADIA, S ;
KRISHNAN, B ;
WANG, CJ ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911
[8]  
Grubbs R.H., 2007, COMPREHENSIVE ORGANO, V11, P179
[9]   Cuprous chloride accelerated Stille reactions. A general and effective coupling system for sterically congested substrates and for enantioselective synthesis [J].
Han, XJ ;
Stoltz, BM ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7600-7605
[10]   Ring-rearrangement metathesis [J].
Holub, Nicole ;
Blechert, Siegfried .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (09) :1064-1082