Progress towards the total synthesis of apoptolidin /
Apoptolidin (I) was first isolated in 1997 by Hayakawa and co-workers from Nocardiopsis sp. soil bacteria. This polyketide natural product was demonstrated to be a specific apoptosis inducer in cells transformed with the adenovirus type 12 E1A oncogene, but not in normal cells. Chapter I of this...
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| Format: | Thesis Book |
| Language: | English |
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[Place of publication not identified] :
[publisher not identified] ;
2002.
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| Online Access: | http://proxy.library.tamu.edu/login?url=http://proquest.umi.com/pqdweb?did=764789721&sid=1&Fmt=2&clientId=2945&RQT=309&VName=PQD |
| Summary: | Apoptolidin (I) was first isolated in 1997 by Hayakawa and co-workers from Nocardiopsis sp. soil bacteria. This polyketide natural product was demonstrated to be a specific apoptosis inducer in cells transformed with the adenovirus type 12 E1A oncogene, but not in normal cells. Chapter I of this dissertation describes the latest findings in the search for apoptolidin's molecular target and the most important contributions towards its total synthesis. Chapter II described the successful synthesis of the C(16)-C(28) fragment of apoptolidin by our group featuring a double diastereoselective Mukaiyama aldol reaction and the recently developed Crimmins' aldol methodology. Chapter III describes the evolution of our apoptolidin end-game strategy. The current approach features two Suzuki cross-coupling reactions to construct the C(5)-C(6) and C(11)-C(12) bonds and a third novel Suzuki coupling to convert the C(6) vinylbromide to the required vinylmethyl using Me-9-BBN. A successful model study is described in Chapter III. |
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| Item Description: | Vita. "Major Subject: Chemistry". |
| Physical Description: | xvii, 302 leaves : illustrations ; 28 cm. Issued also on microfiche from University Microfilm Inc. |
| Bibliography: | Includes bibliographical references (leaves 147-152). |