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Stereoselective synthesis of (-)-tetrodotoxin

Record Type:	Electronic resources : Monograph/item
Title/Author:	Stereoselective synthesis of (-)-tetrodotoxin
Author:	Hinman, Andrew William.
Description:	203 p.
Notes:	Adviser: Justin Du Bois.
Notes:	Source: Dissertation Abstracts International, Volume: 65-04, Section: B, page: 1868.
Contained By:	Dissertation Abstracts International65-04B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3128650
ISBN:	0496759124

Stereoselective synthesis of (-)-tetrodotoxin
Hinman, Andrew William.

Stereoselective synthesis of (-)-tetrodotoxin [electronic resource] - 203 p.

Adviser: Justin Du Bois.

Thesis (Ph.D.)--Stanford University, 2004.

A total synthesis of the potent sodium channel blocker (-)-tetrodotoxin (TTX) is described. The route features two stereospecific C-H insertion reactions using modern catalytic metal carbene and metal nitrene methodologies. These transformations facilitate the installation of the tetrasubstituted stereocenters at C6 and C8a by selective elaboration of trisubstituted stereocenters. In the studies described herein, C-H insertion chemistry is demonstrated to be a powerful tool for simplifying complex problems in synthesis. Other novel transformations employed for the synthesis of TTX include a NaOAc-promoted dialkyloxalacetate aldol reaction, a diastereo- and chemoselective reduction of a vinylogous anhydride, and a selenium-catalyzed allylic oxidation. The latter was based on a protocol developed by Barton and was further investigated to establish scope and limitations. These studies resulted in a 32-step synthesis of (-)-tetrodotoxin from the optically pure starting material D-isoascorbic acid.

ISBN: 0496759124Subjects--Topical Terms:

193634
Chemistry, Organic.

Stereoselective synthesis of (-)-tetrodotoxin
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520 # $a A total synthesis of the potent sodium channel blocker (-)-tetrodotoxin (TTX) is described. The route features two stereospecific C-H insertion reactions using modern catalytic metal carbene and metal nitrene methodologies. These transformations facilitate the installation of the tetrasubstituted stereocenters at C6 and C8a by selective elaboration of trisubstituted stereocenters. In the studies described herein, C-H insertion chemistry is demonstrated to be a powerful tool for simplifying complex problems in synthesis. Other novel transformations employed for the synthesis of TTX include a NaOAc-promoted dialkyloxalacetate aldol reaction, a diastereo- and chemoselective reduction of a vinylogous anhydride, and a selenium-catalyzed allylic oxidation. The latter was based on a protocol developed by Barton and was further investigated to establish scope and limitations. These studies resulted in a 32-step synthesis of (-)-tetrodotoxin from the optically pure starting material D-isoascorbic acid.
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