A general scaffold for the synthesis of cysiherbaine and its analogues

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Title: A general scaffold for the synthesis of cysiherbaine and its analogues
Author: Chang Won Kang
Abstract: Dysiherbaine 1 and a select number of structurally related compounds have been shown to have selective effects on ionotropic glutamate receptors (iGluRs ) . iGluRs are essential components in the central nervous system (CNS ) ; playing an important role in memory and learning . They also play a role in a number of neurological disorders , including schizophrenia , epilepsy , Rasmussen¡¯s encephalitis and stroke ; along with neurodegenerative disorders such as Alzheimer¡¯s , Parkinson¡¯s and Huntington¡¯s diseases . This dissertation describes the synthesis of key molecule 4 and future directions for its use . The molecule will serve as the branch point for the synthesis of other analogues . We designed a 12 step route to this molecule that utilizes highly stereo - and regioselective reactions . The molecule 4 will provide dysiherbaine and a series of analogues without having to design a new total synthesis for each analogue . While there are a number of syntheses of dysiherbaine reported , they are not appropriate for the easy variation of the important C8 -amino C9 -alcohol pharmacophore . The molecule 4 has a double bond between the C8 and C9 position as the key reactive functional group . The principal reactivity that will be used to synthesize derivatives of this molecule involves the double bond . Addition reactions of electrophilic reagents to the double bond are the most typical , and include hydroxylation , hydrogenation , halogenation , alkylation , amination , etc . This will be a unique and simple way to make dysiherbaine and analogues with just few steps from molecule 4 . Finally , this work will provide unique molecules that will enhance the understanding of the structure and function of ionotropic Glu receptors in the CNS .
URI: http : / /hdl .handle .net /2152 .3 /62
Date: 2008-12-03


A general scaffold for the synthesis of cysiherbaine and its analogues. Doctoral dissertation, The University of Texas Medical Branch. Available electronically from http : / /hdl .handle .net /2152 .3 /62 .

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