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Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A.
Author:	Peterson, Gretchen Susan.
Description:	159 p.
Notes:	Adviser: David A. Evans.
Notes:	Source: Dissertation Abstracts International, Volume: 65-05, Section: B, page: 2424.
Contained By:	Dissertation Abstracts International65-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3131953
ISBN:	0496791931

Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A.
Peterson, Gretchen Susan.

Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A.[electronic resource] - 159 p.

Adviser: David A. Evans.

Thesis (Ph.D.)--Harvard University, 2004.

*Please refer to dissertation for diagrams.

ISBN: 0496791931Subjects--Topical Terms:

193634
Chemistry, Organic.

Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A.
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245 1 0 $a Studies toward the total syntheses of teicoplanin aglycon and cyclomarin A. $h [electronic resource]
300 $a 159 p.
500 $a Adviser: David A. Evans.
500 $a Source: Dissertation Abstracts International, Volume: 65-05, Section: B, page: 2424.
502 $a Thesis (Ph.D.)--Harvard University, 2004.
520 # $a *Please refer to dissertation for diagrams.
520 # $a 1. Studies toward the synthesis of the teicoplanin aglycon M(1,3) macrocycle. A nucleophilic aromatic substitution (SNAr) reaction closed linear peptide 55 to provide the M(1,3) macrocycle precursor 91. Arylglycine 1 was incorporated as an alpha-keto amide to avoid racemization during the biaryl etherification. Stereoselective installation of the amine terminus was then investigated on macrocycle 91. The constituent amino acids were each synthesized using methodology developed in the Evans laboratories.*
520 # $a 2. Synthesis of the teicoplanin aglycon M(4,6)(5,7) bicycle. The M(4,6)(5,7) bicyclic fragment was synthesized for completion of the teicoplanin aglycon total synthesis. An SNAr macrocyclization of the M(4,6) ring proceeded with good atropdiastereoisomer control. After several refunctionalizations, removal of the methyl ether protecting groups allowed for thermal equilibration of 185 to the natural M(5,7) atropisomer 186. Reprotection of the phenols as methyl ether 189 prevented the development of undesired M(1,3) atropisomers during the final steps of the total synthesis.*
520 # $a 3. Studies toward the total synthesis of cyclomarin A. The total synthesis of cyclomarin A 195 has begun with the efficient construction of three non-proteogenic amino acid components: 210, 211, and 212. Several options for the synthesis of beta-hydroxytryptophan 209 have been evaluated. Routes for the completion of cyclomarin A, including peptide assembly and macrolactamization, have been detailed.*
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