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Propargylguanidine hydroamination ap...

Bhonde, Vasudev Ramchandra.

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Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products./
Author:	Bhonde, Vasudev Ramchandra.
Description:	481 p.
Notes:	Source: Dissertation Abstracts International, Volume: 75-08(E), Section: B.
Contained By:	Dissertation Abstracts International75-08B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3617065
ISBN:	9781303841767

Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products.
Bhonde, Vasudev Ramchandra.

Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products. - 481 p.

Source: Dissertation Abstracts International, Volume: 75-08(E), Section: B.

Thesis (Ph.D.)--The University of Utah, 2014.

This item must not be sold to any third party vendors.

Saxitoxin (STX) and its natural and unnatural analogues have been used as a biomedical tool in understanding the structure and function of the voltage gated sodium channels (NaV). Despite its extreme neurotoxicity, STX has been studied for the last six decades in various disciplines. After its structure elucidation in 1975, it became an attractive target in the chemical community due to its fascinating structure, the arrangement of heteroatom-rich tricyclic skeleton and its highly polar nature. To date, six total syntheses of this tricyclic bis-guanidine alkaloid were reported with each having its own distinct flavor, as discussed in Chapter 1 and Chapter 2.

ISBN: 9781303841767Subjects--Topical Terms:

523952
Organic chemistry.

Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products.
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020 $a 9781303841767
035 $a (MiAaPQ)AAI3617065
035 $a AAI3617065
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100 1 $a Bhonde, Vasudev Ramchandra. $3 3172805
245 1 0 $a Propargylguanidine hydroamination application to the total synthesis of bis-guanidine natural products.
300 $a 481 p.
500 $a Source: Dissertation Abstracts International, Volume: 75-08(E), Section: B.
500 $a Adviser: Ryan E. Looper.
502 $a Thesis (Ph.D.)--The University of Utah, 2014.
506 $a This item must not be sold to any third party vendors.
506 $a This item must not be added to any third party search indexes.
520 $a Saxitoxin (STX) and its natural and unnatural analogues have been used as a biomedical tool in understanding the structure and function of the voltage gated sodium channels (NaV). Despite its extreme neurotoxicity, STX has been studied for the last six decades in various disciplines. After its structure elucidation in 1975, it became an attractive target in the chemical community due to its fascinating structure, the arrangement of heteroatom-rich tricyclic skeleton and its highly polar nature. To date, six total syntheses of this tricyclic bis-guanidine alkaloid were reported with each having its own distinct flavor, as discussed in Chapter 1 and Chapter 2.
520 $a In our synthesis of STX, we utilized a regiodivergent propargylguanidine hydroamination strategy to construct the bis-guanidine skeleton. A sequential Ag(I)-mediated oxidative cyclization strategy was employed which makes this synthesis atom-economical wherein two C-N bonds, one C-O bond, three rings are constructed in a single operation with excellent diastereo and regiocontrol.
520 $a The utilization of the regiodivergent pyrrolidine ring annulation executed the parent natural product as well as the unnatural analogues of STX in highly step-economical fashion.
520 $a The Type III Secretion System (T3SS) is an emerging target for fighting infectious diseases. The significant inhibitory activity of guadinomine B towards T3SS is an exciting challenge for the synthesis of this natural product. Our efforts toward the synthesis of guadinomine B involved a convergent approach in obtaining the truncated analogues to find the active pharmacophore/s associated with the inhibition of T3SS.
520 $a The Aromatic hydrocarbon receptor (Ahr) is a ligand-dependant transcription factor, which often gets activated by the various exogenous polyaromatic hydrocarbons. In collaboration with Welm lab, the use of DNA microarray gene expression data suggested the activation of Ahr through upregulation of the desmosome cadherins. The use of forward chemical genetic screening helped in identifying the novel molecular pathways and finding novel modulators for the dynamic nature of the branching morphogenesis.
590 $a School code: 0240.
650 4 $a Organic chemistry. $3 523952
650 4 $a Biology. $3 522710
650 4 $a Chemistry. $3 516420
690 $a 0490
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710 2 $a The University of Utah. $b Chemistry. $3 2103671
773 0 $t Dissertation Abstracts International $g 75-08B(E).
790 $a 0240
791 $a Ph.D.
792 $a 2014
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3617065