An efficient strategy for the iterative synthesis of a trans-fused polytetrahydropyran ring system via SmI2-induced reductive intramolecular cyclization

被引:103
作者
Hori, N [1 ]
Matsukura, H [1 ]
Matsuo, G [1 ]
Nakata, T [1 ]
机构
[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan
关键词
samarium diiodide; radical reaction; cyclization; tetrahydropyrans;
D O I
10.1016/S0040-4039(99)00301-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient strategy for the iterative synthesis of a trans-fused polytetrahydropyran ring system was developed. The new iterative method involves SmI2-induced reductive intramolecular cyclization of an aldehyde and a beta-alkoxy acrylate as the key step, producing a 2,3-trans-tetrahydropyran ring. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2811 / 2814
页数:4
相关论文
共 39 条
[1]   USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].
ALVAREZ, E ;
CANDENAS, ML ;
PEREZ, R ;
RAVELO, JL ;
MARTIN, JD .
CHEMICAL REVIEWS, 1995, 95 (06) :1953-1980
[2]   STEREOSELECTIVE RADICAL CYCLIZATION FOR THE SYNTHESIS OF BICYCLIC HIGHER-CARBON SUGARS - SYNTHESIS OF THE SUGAR MOIETY OF OCTOSYL ACIDS [J].
ARAKI, Y ;
ENDO, T ;
ARAI, Y ;
TANJI, M ;
ISHIDO, Y .
TETRAHEDRON LETTERS, 1989, 30 (21) :2829-2832
[3]   LANTHANIDE INDUCED INTRAMOLECULAR COUPLING OF ALDEHYDES AND KETONES WITH ELECTRON-DEFICIENT OLEFINS [J].
ENHOLM, EJ ;
TRIVELLAS, A .
TETRAHEDRON LETTERS, 1989, 30 (09) :1063-1066
[4]   SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES [J].
ENHOLM, EJ ;
TRIVELLAS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6463-6465
[5]   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
[6]   An iterative approach to biologically important fused polycyclic ethers via acyl radical cyclizations [J].
Evans, PA ;
Roseman, JD ;
Garber, LT .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4880-4881
[7]   SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE [J].
FUKUZAWA, S ;
NAKANISHI, A ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1669-1675
[8]   REDUCTIVE COUPLING OF KETONES OR ALDEHYDES WITH ELECTRON-DEFICIENT ALKENES PROMOTED BY SAMARIUM DIIODIDE [J].
FUKUZAWA, S ;
NAKANISHI, A ;
FUJINAMI, T ;
SAKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (08) :624-625
[9]   STEREOCONTROLLED SYNTHESIS OF THE HEMIBREVETOXIN RING-SYSTEM VIA AN ALLYLIC TIN METHOD [J].
KADOTA, I ;
MATSUKAWA, Y ;
YAMAMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (21) :1638-1641
[10]  
KAGAN HB, 1990, NEW J CHEM, V14, P453