Domino Knoevenagel hetero-Diels-Alder reactions:: a stereoselective synthesis of sugar fused furo[3,2-b]pyrano[4,3-d]pyran derivatives

被引：36

作者：

Yadav, JS ^{[1
]}

Reddy, BVS

Narsimhaswamy, D

Lakshmi, PN

Narsimulu, K

Srinivasulu, G

Kunwar, AC

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Ctr Nucl Magnet Resonance, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期

关键词：

domino Knoevenagel hetero-Diels-Alder reaction; 1,3-diones; sugar aldehyde; cis-annelated polycyclic heterocycles;

D O I：

10.1016/j.tetlet.2004.02.149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The O-prenyl derivative of a sugar aldehyde derived from D-glucose undergoes smooth intramolecular domino Knoevenagel hetero-Diels-Alder reactions with 1,3-diones to afford a novel class of carbohydrate analogues, cis-fused furopyranopyrans in good yields with a high degree of chemoselectivity. The stereochemistry of the products was assigned by NMR. (C) 2004 Published by Elsevier Ltd.

引用

页码：3493 / 3497

页数：5

共 2 条

[1] Domino Knoevenagel-hetero-Diels-Alder reactions: a stereoselective synthesis of sugar-annulated furo[3,2-b] pyrano[4,3-d]pyran derivatives
Yadav, J. S.
Reddy, B. V. Subba
Gopal, A. V. Hara
Rao, R. Nageshwar
Somaiah, R.
Reddy, P. Purushotham
Kunwar, A. C.
TETRAHEDRON LETTERS, 2010, 51 (17) : 2305 - 2308
[2] Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium
Majumdar, K. C.
Taher, Abu
Ponra, Sudipta
TETRAHEDRON LETTERS, 2010, 51 (17) : 2297 - 2300

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