Convergent and stereoselective method for synthesis of O-linked oxepane ring system by intramolecular radical cyclization

被引:63
作者
Sasaki, M [1 ]
Inoue, M [1 ]
Noguchi, T [1 ]
Takeichi, A [1 ]
Tachibana, K [1 ]
机构
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 113, Japan
关键词
D O I
10.1016/S0040-4039(98)00338-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the construction of O-linked oxepane ring system is described. The present method involves regioselective acetal cleavage by i-Bu2AlSePh and intramolecular radical cyclization by use of beta-alkoxyacrylate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2783 / 2786
页数:4
相关论文
共 38 条
[1]   SYNTHESIS OF UNSATURATED TRANS-FUSED POLYETHER FRAMEWORKS VIA O-LINKED OXACYCLES - A CONVERGENT APPROACH [J].
ALVAREZ, E ;
DIAZ, MT ;
HANXING, L ;
MARTIN, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (04) :1437-1438
[2]   A concise synthesis of ortho-condensed oxane-oxene, oxepene, oxocene and oxonene ring systems [J].
Alvarez, E ;
Delgado, M ;
Diaz, MT ;
Liu, HX ;
Perez, R ;
Martin, JD .
TETRAHEDRON LETTERS, 1996, 37 (16) :2865-2868
[3]  
Atsuta H, 1997, SYNLETT, P307
[4]  
BIDARD JN, 1984, J BIOL CHEM, V259, P8353
[5]   Vinylogous sulfonates as radical acceptors for the stereoselective synthesis of cyclic ethers [J].
Evans, PA ;
Manangan, T .
TETRAHEDRON LETTERS, 1997, 38 (47) :8165-8168
[6]   Stereoselective synthesis of the 2,6-disubstituted tetrahydropyran-3-ol of the potent antitumor agent mucocin via an acyl radical cyclization [J].
Evans, PA ;
Roseman, JD .
TETRAHEDRON LETTERS, 1997, 38 (30) :5249-5252
[7]   Stereoselective construction of cyclic ethers via intramolecular acyl radical cyclizations: A practical solution to decarbonylation [J].
Evans, PA ;
Roseman, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2252-2253
[8]  
EVANS PA, 1996, J ORG CHEM, V61, P4840
[9]  
HOSOKAWA S, 1995, SYNLETT, P1179
[10]   ORGANIC-SYNTHESIS WITH TRIALKYLPHOSPHINE CATALYSTS - CONJUGATE ADDITION OF ALCOHOLS TO ALPHA,BETA-UNSATURATED ALKYNIC ACID-ESTERS [J].
INANAGA, J ;
BABA, Y ;
HANAMOTO, T .
CHEMISTRY LETTERS, 1993, (02) :241-244