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
KAWATSURA, M
MATSUDA, F
SHIRAHAMA, H
[J]. 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
KOZIKOWSKI, AP
GHOSH, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) : 3017 - 3019
[16] Radical cyclization of beta-alkoxyacrylates: Stereoselective synthesis of (-)-trans-kumausyne
Lee, E
Yoo, SK
Cho, YS
Cheon, HS
Chong, YH
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7757 - 7758
[17] TOTAL SYNTHESIS OF DACTOMELYNES
LEE, E
PARK, CM
YUN, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (30) : 8017 - 8018
[18] BETA-ALKOXYACRYLATES IN RADICAL CYCLIZATIONS - REMARKABLY EFFICIENT OXACYCLE SYNTHESIS
LEE, E
TAE, JS
LEE, C
PARK, CM
[J]. TETRAHEDRON LETTERS, 1993, 34 (30) : 4831 - 4834
[19] Diastereoselective radical cyclization of chiral beta-alkoxyacrylates
Lee, E
Jeong, JW
Yu, Y
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7765 - 7768
[20] FUSED OXACYCLE SYNTHESIS VIA RADICAL CYCLIZATION OF BETA-ALKOXYACRYLATES
LEE, E
TAE, JS
CHONG, YH
PARK, YC
YUN, M
KIM, S
[J]. TETRAHEDRON LETTERS, 1994, 35 (01) : 129 - 132

← 1 2 3 4 →