Stereoselective syntheses of trans-fused 6,6-and 6,7-membered ether ring systems having an angular methyl group based on SmI2-induced reductive intramolecular cyclization

被引：69

作者：

Matsuo, G ^{[1
]}

Hori, N ^{[1
]}

Nakata, T ^{[1
]}

机构：

[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 50期

关键词：

samarium dioxide; cyclization; tetrahydropyrans; oxepanes;

D O I：

10.1016/S0040-4039(99)01861-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective syntheses of trans-fused 6,6- and 6,7-membered ether ring systems having an angular methyl group were achieved based on SmI2-induced reductive intramolecular cyclizations of an aldehyde or a methyl ketone and a beta-alkoxy acrylate. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8859 / 8862

页数：4

共 16 条

[1]

FEI K, 1992, CHEM LETT, P1587

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

Hori, N ;

Matsukura, H ;

Matsuo, G ;

Nakata, T .

TETRAHEDRON LETTERS, 1999, 40 (14) :2811-2814

[3] Efficient synthesis of trans-fused polycyclic ethers including tetrahydropyrans and oxepanes based on SmI2-induced reductive cyclization [J].

Hori, N ;

Matsukura, H ;

Nakata, T .

ORGANIC LETTERS, 1999, 1 (07) :1099-1101

[4]

KADOTA I, 1993, J CHEM SOC CHEM COMM, P1368

[5]

KAGAN HB, 1990, NEW J CHEM, V14, P453

[6] A NOVEL METHOD FOR COPPER(I)-CATALYZED COUPLING REACTIONS OF TRIFLATES WITH GRIGNARD-REAGENTS [J].

KOTSUKI, H ;

KADOTA, I ;

OCHI, M .

TETRAHEDRON LETTERS, 1989, 30 (10) :1281-1284

[7] Sequencing reactions with samarium(II) iodide [J].

Molander, GA ;

Harris, CR .

CHEMICAL REVIEWS, 1996, 96 (01) :307-338

[8] APPLICATION OF LANTHANIDE REAGENTS IN ORGANIC-SYNTHESIS [J].

MOLANDER, GA .

CHEMICAL REVIEWS, 1992, 92 (01) :29-68

[9] A new strategy for the reiterative synthesis of trans-fused tetrahydropyrans via alkylation of oxiranyl anion and 6-endo cyclization [J].

Mori, Y ;

Yaegashi, K ;

Furukawa, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8158-8159

[10] NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF OXOCENES [J].

NICOLAOU, KC ;

DUGGAN, ME ;

HWANG, CK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2468-2469

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