The Study of Intramolecular Acylsilane Radical Cyclizations Based on Carbohydrate Templates
Date Issued
2009
Date
2009
Author(s)
Kuo, Yu-Hsien
Abstract
In this thesis, we described the synthesis of four kinds of acylsilanes that are derived from xylose, mannose, and glucose. Our method conserved the orginal stereochemistry of carbohydrate molecules in this route. The reducing ends were converted to an acylsilane functionality whereas the non-reducing ends were transformed into a halide. All the secondary hydroxyl groups were protected as ethers. By using these carbohydrate-derived acylsilanes, the radical cyclizations were accomplished. It is the first case about radical cyclizations of acylsilanes using hexoses as templates. However, the cyclization efficiencies are not as good as the pentose system. Combined with previous research, we disscussed the influence of the substituents on the stereoselectivity of radical cyclizations. Finally, to demonstrate the synthetic utility of our synthetic method, one of the polyhydroxylated cyclopentanes was converted to an amino sugar mimics that may exhibit useful biological activities.
Subjects
radic
acylsilane
carbohydrate
Type
thesis
File(s)![Thumbnail Image]()
Loading...
Name
ntu-98-R96223105-1.pdf
Size
23.32 KB
Format
Adobe PDF
Checksum
(MD5):633637425ebb360a04d0da498b8bb36f