I. Chemoselective Dehydrative Glycosylation With Application Toward Oligosaccharide Synthesis. II. Sulfide-Mediated Direct Glycosylation of C(1)-Hydroxyl Glycosyl Donors. III. Studies Toward the Total Synthesis of Auriside A
Nguyen, Hien Minh
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Permalink
https://hdl.handle.net/2142/84128
Description
Title
I. Chemoselective Dehydrative Glycosylation With Application Toward Oligosaccharide Synthesis. II. Sulfide-Mediated Direct Glycosylation of C(1)-Hydroxyl Glycosyl Donors. III. Studies Toward the Total Synthesis of Auriside A
Author(s)
Nguyen, Hien Minh
Issue Date
2003
Doctoral Committee Chair(s)
Gin, David Y.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
Our efforts for the development of novel strategies for the total synthesis of auriside A are present in the third part of the dissertation. The hemiacetal disaccharide portion of auriside A is successfully synthesized. The convergent synthesis of the auriside aglycon component is accomplished in 17 linear steps using the Mukaiyama aldol reaction, the intramolecular Mitsunobu macrolactonization, and the Julia olefination for the installation of the C(5)-stereogenic center, the 14-membered macrolactone, and the conjugated bromodiene moiety, respectively.
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