A Total Synthesis of Protoberberine Alkaloids

Fichtner, Harry Robert

Please use this identifier to cite or link to this item: http://hdl.handle.net/11375/7657

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DC Field	Value	Language
dc.contributor.advisor	MacLean, D. B.	en_US
dc.contributor.author	Fichtner, Harry Robert	en_US
dc.date.accessioned	2014-06-18T16:40:02Z	-
dc.date.available	2014-06-18T16:40:02Z	-
dc.date.created	2009-07-12	en_US
dc.date.issued	1980-05	en_US
dc.identifier.other	opendissertations/292	en_US
dc.identifier.other	1322	en_US
dc.identifier.other	894812	en_US
dc.identifier.uri	http://hdl.handle.net/11375/7657	-
dc.description.abstract	<p>The synthesis of protoberberines developed in this laboratory by Kiparissides has been studied in greater detail. The key intermediate in this synthesis is formed by the condensation of 3,4-dihydro-6,7-dimethoxy-N-(2,3-dimethoxybenzyl)-isoquinolinium chloride with the anion of methyl methylthiomethylsulfoxide. Careful chromatography of the product has established that it is a complex mixture of diastereomers. The separated fractions were individually cyclized to dihydropalmatine chloride, which was isolated in crystalline form directly from the reaction mixture. This quarternary salt was reduced directly to tetrahydropalmatine, and also used in the synthesis of corydaline.</p> <p>This work has also shown that isoquinolines may be substituted for 3,4-dihydroisoquinolines as starting materials in the synthetic sequence.</p>	en_US
dc.subject	Chemistry	en_US
dc.subject	Chemistry	en_US
dc.title	A Total Synthesis of Protoberberine Alkaloids	en_US
dc.type	thesis	en_US
dc.contributor.department	Chemistry	en_US
dc.description.degree	Master of Science (MS)	en_US
Appears in Collections:	Open Access Dissertations and Theses

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