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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.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Studies directed toward the total synthesis of (-)-Apoptolidin A./
作者:	Srinivasan, Venkatesan.
面頁冊數:	456 p.
附註:	Adviser: Robert K. Boeckman, Jr.
Contained By:	Dissertation Abstracts International70-01B.
標題:	Biology, Cell. -
電子資源:	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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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.
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791 $a Ph.D.
792 $a 2009
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