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Date of Award
2002
Document Type
Dissertation - Pacific Access Restricted
Degree Name
Doctor of Philosophy (Ph.D.)
Department
Chemistry
First Advisor
Paul Gross
First Committee Member
Patrick Jones
Second Committee Member
Xiaoling Li
Third Committee Member
Vyacheslav Samoshin
Fourth Committee Member
Donald Wedegaertner
Abstract
C-glycosides play important roles in biological processes. Synthetic efforts to prepare carbohydrate mimetics—C-glycosides were undertaken. This thesis introduces the total syntheses of C-glycosides by starting with two cycloaddition reactions. The [4+2] reaction of 1,3-pentadiene with glyoxylic acid and subsequent reactions afforded five C-pyranosides. The [4+3] cycloaddition of furan and pentachloroacetone and subsequent reactions provided C-furanosides and C-pyranosides. A new type of C-disaccharide mimetic coupled by an amide bond was synthesized. This thesis describes how bromolactonization, stereoselective Beckmann rearrangement and stereoselective dechlorination were used in a new way to fulfill the research goal. This dissertation provides efficient ways to synthesize carborhydrate mimetics from cheap, easily available non-natural materials.
Pages
115
ISBN
9780493646251 , 0493646256
Recommended Citation
Lu, Jun. (2002). The total synthesis of C-glycosides by cycloaddition reactions. University of the Pacific, Dissertation - Pacific Access Restricted. https://scholarlycommons.pacific.edu/uop_etds/2709
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