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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

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

页码：2811 / 2814

页数：4

共 39 条

[11]

Kawatsura M, 1996, SYNLETT, P373

[12] SAMARIUM(II) IODIDE PROMOTED INTERMOLECULAR KETONE OLEFIN COUPLINGS CHELATION-CONTROLLED BY ALPHA-HYDROXYL GROUPS [J].

KAWATSURA, M ;

MATSUDA, F ;

SHIRAHAMA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6900-6901

[13]

KITO M, 1993, SYNLETT, P158

[14]

Kito M, 1996, SYNLETT, P1057

[15] METHODS FOR PYRANOANNULATION - AN APPROACH TO A NEW CLASS OF POLYETHERS [J].

KOZIKOWSKI, AP ;

GHOSH, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3017-3019

[16] Radical cyclization of beta-alkoxyacrylates: Stereoselective synthesis of (-)-trans-kumausyne [J].

Lee, E ;

Yoo, SK ;

Cho, YS ;

Cheon, HS ;

Chong, YH .

TETRAHEDRON LETTERS, 1997, 38 (44) :7757-7758

[17] TOTAL SYNTHESIS OF DACTOMELYNES [J].

LEE, E ;

PARK, CM ;

YUN, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (30) :8017-8018

[18] BETA-ALKOXYACRYLATES IN RADICAL CYCLIZATIONS - REMARKABLY EFFICIENT OXACYCLE SYNTHESIS [J].

LEE, E ;

TAE, JS ;

LEE, C ;

PARK, CM .

TETRAHEDRON LETTERS, 1993, 34 (30) :4831-4834

[19] Diastereoselective radical cyclization of chiral beta-alkoxyacrylates [J].

Lee, E ;

Jeong, JW ;

Yu, Y .

TETRAHEDRON LETTERS, 1997, 38 (44) :7765-7768

[20] FUSED OXACYCLE SYNTHESIS VIA RADICAL CYCLIZATION OF BETA-ALKOXYACRYLATES [J].

LEE, E ;

TAE, JS ;

CHONG, YH ;

PARK, YC ;

YUN, M ;

KIM, S .

TETRAHEDRON LETTERS, 1994, 35 (01) :129-132

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