Highly functionalized glyco-conjugated hexahydroazepindiones from saccharide imides via the Norrish type II reaction |
| |
Authors: | Stark Markus Thiem Joachim |
| |
Affiliation: | Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany. |
| |
Abstract: | Starting from readily available protected 6-tosylates of D-glucose and D-mannose in both their pyranoside and furanoside forms as well as 6-tosylates of alpha-D-galactopyranose, the corresponding primary succinimido derivatives were obtained in good yield by nucleophilic displacement with potassium succinimide. These imido sugars were photochemically transformed into hexahydroazepindione derivatives such as by means of a Norrish type II reaction. As expected, the intramolecular alkylation proceeded via an 1,6 H-abstraction leading to a stabilized diradical. The regiochemistry of the photoreaction was controlled by configurational, conformational and electronic features and was sometimes influenced by the protecting groups. Using this route, a facile approach to a novel class of highly functionalized sugar derived heterocycles was developed. |
| |
Keywords: | Hexahydroazepinediones Saccharides Imides Norrish type II |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|