Intramolecular Diels-Alder reaction of dinitro-olefin derivatives of furan for the preparation of a versatile tool: 3,7-dinitro-11-oxatricycloundec-9-ene

被引：34

作者：

Sader-Bakaouni, L ^{[1
]}

Charton, O ^{[1
]}

Kunesch, N ^{[1
]}

Tillequin, F ^{[1
]}

机构：

[1] Univ Paris 05, Fac Sci Pharmaceut & Biol, Lab Pharmacognosie, URA CNRS 1310, F-75270 Paris 06, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)10411-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recurrent additions of nitromethane on furfuraldehyde followed by an intramolecular Diels-Alder reaction allowed the obtention of the title compound 1 in good yield with excellent stereoselectivity. Aromatization, ether cleavage and stereocontrolled oxidation reactions give evidence of the synthetic versatility of this adduct in the preparation of ergot alkaloids and valienamine bicyclic analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1773 / 1782

页数：10

共 62 条

[1]

[Anonymous], [No title captured], Patent No. 3976639

[2] CHEMOSELECTIVE SYNTHESIS OF FUNCTIONALIZED CONJUGATED NITROALKENES [J].