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Development of ligand assisted asymm...

Cappiello, John Robert.

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Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B./
Author:	Cappiello, John Robert.
Description:	198 p.
Notes:	Adviser: Arun K. Ghosh.
Contained By:	Dissertation Abstracts International61-07B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9978650
ISBN:	9780599846524

Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B.
Cappiello, John Robert.

Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B. - 198 p.

Adviser: Arun K. Ghosh.

Thesis (Ph.D.)--University of Illinois at Chicago, 2000.

This thesis describes the development of the C2-symmetric bis(oxazoline) ligand derived from cis-1-amino-2-indanol and the progress toward the synthesis of the antiulcer agent AI-77-B.

ISBN: 9780599846524Subjects--Topical Terms:

516206
Chemistry, Organic.

Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B.
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020 $a 9780599846524
035 $a (UMI)AAI9978650
035 $a AAI9978650
040 $a UMI $c UMI
100 1 $a Cappiello, John Robert. $3 1271817
245 1 0 $a Development of ligand assisted asymmetric synthetic methodology and synthetic progress toward AI-77-B.
300 $a 198 p.
500 $a Adviser: Arun K. Ghosh.
500 $a Source: Dissertation Abstracts International, Volume: 61-07, Section: B, page: 3592.
502 $a Thesis (Ph.D.)--University of Illinois at Chicago, 2000.
520 $a This thesis describes the development of the C2-symmetric bis(oxazoline) ligand derived from cis-1-amino-2-indanol and the progress toward the synthesis of the antiulcer agent AI-77-B.
520 $a In part one, the development of the conformationally constrained bis(oxazoline) ligand as a chiral catalyst for Diels-Alder reactions is presented. The reaction of cyclopentadiene with various bidentate dienophiles in the presence of 4--10 mol% metal-bis(oxazoline) complexes afforded excellent endo/ exo selectivity as well as endo enantioselectivity (95--99% ee) and isolated yields.
520 $a Part two describes our investigations of chiral metal-bis(oxazoline) derived Lewis acid catalysts in the asymmetric hetero Diels-Alder reaction of Danishefsky's diene with glyoxylate esters as well as other bidentate aldehydes. Among various ligand-metal complexes examined, conformationally constrained Cu(II)-bis(oxazoline) derived from cis-1-amino-2-indanol proved to be most effective with selectivities up to 72% ee and good yields. This catalytic process provided a convenient access to synthetically useful, versatile dihydropyranones. Particularly, cyclocondensation with benzyloxyacetaldehyde provided excellent selectivity in up to 87% ee. This catalytic methodology was used in the synthesis of a segment of the natural product laulimalide as well as the synthesis of nonpeptidal ligands for the HIV binding site.
520 $a The synthesis of the dihydroisocoumarin moiety and our synthetic progress toward the hydroxylated amino acid side chain of the gastroprotective natural product AI-77-B is presented in part three. The key step in the 'western' fragment is a regiospecific Diels-Alder reaction. Application of a stereoselective syn-Aldol reaction and a Curtius rearrangement was used in the partial synthesis of the 'eastern' portion. Two of the three chiral centers were provided by these key steps.
590 $a School code: 0799.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
650 4 $a Health Sciences, Pharmacology. $3 1017717
690 $a 0419
690 $a 0490
690 $a 0491
710 2 0 $a University of Illinois at Chicago. $3 1020478
773 0 $t Dissertation Abstracts International $g 61-07B.
790 $a 0799
790 1 0 $a Ghosh, Arun K., $e advisor
791 $a Ph.D.
792 $a 2000
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9978650