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Studies towards the total synthesis ...

Ciurea, Diana V.

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Studies towards the total synthesis of ristocetin A and orienticin C aglycones.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Studies towards the total synthesis of ristocetin A and orienticin C aglycones./
Author:	Ciurea, Diana V.
Description:	198 p.
Notes:	Adviser: Anthony J. Pearson.
Contained By:	Dissertation Abstracts International68-09B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3285349
ISBN:	9780549258872

Studies towards the total synthesis of ristocetin A and orienticin C aglycones.
Ciurea, Diana V.

Studies towards the total synthesis of ristocetin A and orienticin C aglycones. - 198 p.

Adviser: Anthony J. Pearson.

Thesis (Ph.D.)--Case Western Reserve University, 2008.

*Please refer to dissertation for diagrams.

ISBN: 9780549258872Subjects--Topical Terms:

516206
Chemistry, Organic.

Studies towards the total synthesis of ristocetin A and orienticin C aglycones.
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005 20110704
008 110704s2008 ||||||||||||||||| ||eng d
020 $a 9780549258872
035 $a (UMI)AAI3285349
035 $a AAI3285349
040 $a UMI $c UMI
100 1 $a Ciurea, Diana V. $3 1282225
245 1 0 $a Studies towards the total synthesis of ristocetin A and orienticin C aglycones.
300 $a 198 p.
500 $a Adviser: Anthony J. Pearson.
500 $a Source: Dissertation Abstracts International, Volume: 68-09, Section: B, page: 5956.
502 $a Thesis (Ph.D.)--Case Western Reserve University, 2008.
520 $a *Please refer to dissertation for diagrams.
520 $a Also, a model study on ruthenium-mediated macrocyclization for the formation of the 16-membered diaryl ether ring 3.32 was investigated, assuring the applicability of this approach to the synthesis of orienticin C aglycone.*
520 $a Chapter three provides details for the construction of the intermediate 3.3, a tripeptido-arene-ruthenium complex, required for a projected synthesis of orienticin C aglycone 3.1.*
520 $a Vancomycin-related glycopeptides constitute a large family of clinically important antibiotics, used as drugs of last resort in treating infections caused by methicillin-resistant Staphylococcus aureus. However, the frequency of vancomycin resistant pathogens has increased significantly over the past decade, prompting an interest in the development of synthetic and semi-synthetic glycopeptides.
520 $a The research work presented in this thesis has been focused on the application of ruthenium-mediated SNAr methodology for the synthesis of diaryl ether linkages both inter- and intramolecularly. As described in chapter two, our efforts first targeted the synthesis of the F-O-G subunit 2.8 of ristocetin A via an intermolecular SNAr reaction between the phenolic OH of the Teoc protected F amino alcohol 2.9 and the chloro substituent of the amino alcohol corresponding to G ring 2.10 . Considerable competing demetalation of the starting material G-ruthenium complex 2.10 occurred during the attempted coupling, which was overcome by stepwise addition of the solid G-ruthenium complex 2.10 to the reaction mixture increasing the yield of this transformation to 66% yield.*
590 $a School code: 0042.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
690 $a 0490
690 $a 0491
710 2 $a Case Western Reserve University. $3 1017714
773 0 $t Dissertation Abstracts International $g 68-09B.
790 $a 0042
790 1 0 $a Pearson, Anthony J., $e advisor
791 $a Ph.D.
792 $a 2008
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3285349