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The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products.
Author:	Shen, Hong.
Description:	1069 p.
Notes:	Adviser: Barry M. Trost.
Notes:	Source: Dissertation Abstracts International, Volume: 64-09, Section: B, page: 4361.
Contained By:	Dissertation Abstracts International64-09B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3104147
ISBN:	0496517155

The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products.
Shen, Hong.

The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products. [electronic resource] - 1069 p.

Adviser: Barry M. Trost.

Thesis (Ph.D.)--Stanford University, 2003.

In ancillary studies, the Pd-catalyzed diyne cycloisomerizations afforded 1,3-dienes, which was employed in synthetic efforts towards (+)-streptazolin. The Ru-catalyzed Alder-ene reactions of internal alkynes and alkenes offered a stereoselective synthesis of trisubstituted alkenes.

ISBN: 0496517155Subjects--Topical Terms:

193634
Chemistry, Organic.

The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products.
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245 1 4 $a The impact of palladium and ruthenium methodologies on strategies for the total syntheses of natural products. $h [electronic resource]
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502 $a Thesis (Ph.D.)--Stanford University, 2003.
520 # $a In ancillary studies, the Pd-catalyzed diyne cycloisomerizations afforded 1,3-dienes, which was employed in synthetic efforts towards (+)-streptazolin. The Ru-catalyzed Alder-ene reactions of internal alkynes and alkenes offered a stereoselective synthesis of trisubstituted alkenes.
520 # $a The Pd-catalyzed intramolecular asymmetric allylic alkylations (AAA) of phenol allylic carbonates provide a facile access to chiral chromans. The unusual acetic acid effect, the influence of olefin geometry and substitution pattern on the ee, and the absolute configuration of the chiral chromans suggest a mechanism involving the cyclization of the more reactive Pd-pi-allyl diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammet conditions). This methodology led to the first enantioselective total synthesis of (+)-clusifoliol, the first enantioselective biomimetic total synthesis of (-)-siccanin, and the enantioselective synthesis of an advanced intermediate towards the total synthesis of rhododaurichromanic acid A.
520 # $a The applications of Pd- and Ru-catalyzed reactions have profound impact on organic synthesis by achieving atom economical transformations that may not be feasible by conventional methods.
520 # $a The development of a Ru-catalyzed [5+2] cycloaddition of vinylcyclopropane alkynes leads to the synthesis of seven-membered ring compounds. The scope, mechanism, diastereoselectivity and regioselectivity have been extensively investigated. The reaction was used for the highly diastereoselective construction of tricyclic compounds containing a seven-membered ring, which demonstrates the potential of this strategy to be applied to the total synthesis of complex natural products. This cycloaddition was also employed in synthetic efforts towards dehydroleucodin.
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