C-linked glycosides are gaining more attention in the chemical community due to their novel structures and importance in carbohydrate and metabolic chemistry. Chemical synthesis of these targets is limited to several methodologies, few of which are convergent, one pot procedures. In this proposal, novel Ni and Pd catalyzed methodology has been proposed to prepare a variety of these biologically C-glycosides. These methods are based on well precedented organometallic reactions and will utilize a variety of mono- and bidentate phosphine ligands to control the chemistry. The synthetic methodology will be illustrated by the rapid, convergent synthesis of alpha-C- mannosyltryptophan, a naturally occurring amino acid in RNase2 from human erythrocytes.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32GM020397-02
Application #
6385136
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Marino, Pamela
Project Start
2001-07-31
Project End
Budget Start
2001-07-31
Budget End
2001-08-30
Support Year
2
Fiscal Year
2001
Total Cost
$5,433
Indirect Cost
Name
Stanford University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
800771545
City
Stanford
State
CA
Country
United States
Zip Code
94305