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Palladium and ruthenium catalysis, applications towards natural product synthesis

Record Type:	Electronic resources : Monograph/item
Title/Author:	Palladium and ruthenium catalysis, applications towards natural product synthesis
Author:	Horne, Daniel Brian.
Description:	455 p.
Notes:	Adviser: Barry M. Trost.
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=3128651
ISBN:	0496759132

Palladium and ruthenium catalysis, applications towards natural product synthesis
Horne, Daniel Brian.

Palladium and ruthenium catalysis, applications towards natural product synthesis [electronic resource] - 455 p.

Adviser: Barry M. Trost.

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

In addition, the versatility of the ruthenium catalyzed [5+2]-cycloaddition of cyclopropyl enynes was investigated. The intermolecular [5+2] reaction of terminal alkynes and 1-vinylcyclopropylethers gives moderate yields of the desired seven-membered ring products. This reaction also proceeds intramolecularly to provide bicyclic systems containing seven-membered rings. The feasibility of applying these examples towards a total synthesis was explored by investigating synthetic approaches towards (-)-frondosin A, a potent anti-inflammatory agent and anti-HIV natural product. Although the synthesis of this natural product was not realized, a carbocyclic [5.3.0]-bicycle containing the necessary stereocenters was synthesized in an enantioselective fashion using the [5+2] cycloaddition reaction.

ISBN: 0496759132Subjects--Topical Terms:

193634
Chemistry, Organic.

Palladium and ruthenium catalysis, applications towards natural product synthesis
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502 $a Thesis (Ph.D.)--Stanford University, 2004.
520 # $a In addition, the versatility of the ruthenium catalyzed [5+2]-cycloaddition of cyclopropyl enynes was investigated. The intermolecular [5+2] reaction of terminal alkynes and 1-vinylcyclopropylethers gives moderate yields of the desired seven-membered ring products. This reaction also proceeds intramolecularly to provide bicyclic systems containing seven-membered rings. The feasibility of applying these examples towards a total synthesis was explored by investigating synthetic approaches towards (-)-frondosin A, a potent anti-inflammatory agent and anti-HIV natural product. Although the synthesis of this natural product was not realized, a carbocyclic [5.3.0]-bicycle containing the necessary stereocenters was synthesized in an enantioselective fashion using the [5+2] cycloaddition reaction.
520 # $a Our initial goal was to develop an efficient and novel method to prepare chiral allylic amines via palladium-catalyzed asymmetric allylic alkylation of amines and butadiene monoxide. The palladium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of a meso-epoxide successfully afforded chiral trans- and cis-2,5-dihydropyrroles, a process involving successive palladium catalyzed asymmetric alkylations of butadiene monoxide and nitrogen nucleophiles. These 2,5-dihydropyrroles are versatile intermediates, allowing entry into the syntheses of a whole host of natural products. The trans-2,5-dihydropyrrole's versatility was demonstrated by the successful synthesis of the glycosidase inhibitors (+)-broussonetine G, and (+)-DMDP, as well as the unnatural amino acid and beta-lactam antibiotic synergist (-)-bulgecinine.
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