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Studies directed toward the total sy...

University of Rochester.

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Studies directed toward the total synthesis of (-)-Apoptolidin A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Studies directed toward the total synthesis of (-)-Apoptolidin A./
Author:	Srinivasan, Venkatesan.
Description:	456 p.
Notes:	Adviser: Robert K. Boeckman, Jr.
Contained By:	Dissertation Abstracts International70-01B.
Subject:	Biology, Cell. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3343620
ISBN:	9780549986508

Studies directed toward the total synthesis of (-)-Apoptolidin A.
Srinivasan, Venkatesan.

Studies directed toward the total synthesis of (-)-Apoptolidin A. - 456 p.

Adviser: Robert K. Boeckman, Jr.

Thesis (Ph.D.)--University of Rochester, 2009.

Synthesis of a bisalkyne subunit via bidirectional chain elongation of a C2 symmetric diepoxide was already developed in our lab. However this route required optimization. An efficient route to the synthesis of bisalkyne subunit is discussed.

ISBN: 9780549986508Subjects--Topical Terms:

1017686
Biology, Cell.

Studies directed toward the total synthesis of (-)-Apoptolidin A.
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020 $a 9780549986508
035 $a (UMI)AAI3343620
035 $a AAI3343620
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100 1 $a Srinivasan, Venkatesan. $3 1064636
245 1 0 $a Studies directed toward the total synthesis of (-)-Apoptolidin A.
300 $a 456 p.
500 $a Adviser: Robert K. Boeckman, Jr.
500 $a Source: Dissertation Abstracts International, Volume: 70-01, Section: B, page: 0304.
502 $a Thesis (Ph.D.)--University of Rochester, 2009.
520 $a Synthesis of a bisalkyne subunit via bidirectional chain elongation of a C2 symmetric diepoxide was already developed in our lab. However this route required optimization. An efficient route to the synthesis of bisalkyne subunit is discussed.
520 $a Progress towards the total synthesis of the cell specific apoptosis inducer (-)-Apoptolidin A is described. Part of this study includes development of a robust procedure for the synthesis of (1) methyl-L-olivomycose, (2) 6-deoxy-4-O-methyl-L-glucose derivative, and (3) D-oleandrose derivative. The disaccharide was obtained by coupling 6-deoxy-4-O-methyl-L-glucose derivative and D-oleandrose derivative under mild conditions. The glycosidation reaction proceeded in excellent yield and with good stereoselectivity.
520 $a Synthesis of a thioester via sequential, titanium-mediated aldol reactions of an acylated oxazolidinethione is described. These aldol reactions proceeded with excellent diastereoselectivity. A shorter and efficient approach to the synthesis of thioester via hetero Diels-Alder reaction has been initiated. These reactions, catalyzed by oxazaborolidines, were highly stereoselective and proceeded in good yield.
520 $a A third generation approach to the synthesis of southern hemisphere of (-)-Apoptolidin A is described. This approach involves addition of a vinylzinc reagent to the aldehyde, followed by an oxidation of the allylic alcohol to an enone. Extensive studies were conducted to improve the regioselectivity of the hydroboration reaction. However, hydroboration of internal alkynes did not provide the desired outcome. Consequently, a hydrozirconation/transmetallation approach was employed. Future studies involving an efficient coupling of northern and southern hemisphere of (-)-apoptolidin A and attachment of sugar units to the macrocycle are discussed.
590 $a School code: 0188.
650 4 $a Biology, Cell. $3 1017686
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
690 $a 0379
690 $a 0490
690 $a 0491
710 2 $a University of Rochester. $3 515736
773 0 $t Dissertation Abstracts International $g 70-01B.
790 $a 0188
790 1 0 $a Boeckman, Robert K., Jr., $e advisor
791 $a Ph.D.
792 $a 2009
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3343620