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Transition metal-catalyzed reactions...

Chung, Cheol Keun.

Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.
Author:	Chung, Cheol Keun.
Description:	369 p.
Notes:	Advisers: Barry M. Trost; Gertrud Tamaki.
Notes:	Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2552.
Contained By:	Dissertation Abstracts International67-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3219251
ISBN:	9780542705892

Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.
Chung, Cheol Keun.

Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide. - 369 p.

Advisers: Barry M. Trost; Gertrud Tamaki.

Thesis (Ph.D.)--Stanford University, 2006.

Alkynes, one of the simplest functional groups in chemistry, are fundamental building blocks in organic synthesis. With the recent advances in transition-metal catalysis and ligand design, the significance of the alkyne functionality is increasingly emphasized in the development of highly selective and atom-economical chemical transformations. The three topics described in this dissertation showcase the versatility of the alkyne functionality in transition metal catalysis.

ISBN: 9780542705892Subjects--Topical Terms:

193634
Chemistry, Organic.

Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.
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100 0 $a Chung, Cheol Keun. $3 264139
245 1 0 $a Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.
300 $a 369 p.
500 $a Advisers: Barry M. Trost; Gertrud Tamaki.
500 $a Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2552.
502 $a Thesis (Ph.D.)--Stanford University, 2006.
520 # $a Alkynes, one of the simplest functional groups in chemistry, are fundamental building blocks in organic synthesis. With the recent advances in transition-metal catalysis and ligand design, the significance of the alkyne functionality is increasingly emphasized in the development of highly selective and atom-economical chemical transformations. The three topics described in this dissertation showcase the versatility of the alkyne functionality in transition metal catalysis.
520 # $a In the presence of an oxovanadium complex, the carbon-carbon triple bond of propargylic alcohols can be transformed to vanadium allenoate complexes via a [3.3]-sigmatropic rearrangement. The allenoate complexes have been successfully utilized in a Mannich-type addition reaction. The initial inactivity has been overcome by modifying the vanadium complex to readily undergo transesterification with propargylic alcohols. Various propargylic alcohols and aryl N-methoxycarbonylimines participate in the reaction providing beta-aryl-alpha,beta-unsaturated ketones with good yield and complete Z-selectivity.
520 # $a The palladium-catalyzed reductive cyclization of bis-alkynes has been successfully applied to the synthesis of (+)-streptazolin. The bis-alkyne precursor was prepared from D-mannitol acetonide via sequential diastereoselective alkynylide addition reactions. The palladium-catalyzed reductive cyclization provided the correct 1,3-diene unit selectively, which has been a major challenge in the synthesis of the molecule. The total synthesis was achieved in 11 steps from commercially available starting materials.
520 # $a Two different metal-catalyzed reactions of alkynes have been utilized in an effort toward the total synthesis of (-)-laulimalide, a potent antitumor macrolide. The dihydropyran ring of the C1--C13 fragment was synthesized chemoselectively by rhodium-catalyzed cycloisomerization from the bis-alkyne substrate, via a vinylidene carbene complex. On the other hand, the second dihydropyran of the C14--C27 fragment was synthesized by ruthenium-catalyzed alkene-alkene coupling followed by palladium-catalyzed intramolecular allylic alkylation. The two main fragments have been combined by using another ruthenium-catalyzed alkene-alkyne coupling reaction, forming the complete carbon framework of laulimalide.
590 $a School code: 0212.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a Stanford University. $3 212607
773 0 # $g 67-05B. $t Dissertation Abstracts International
790 $a 0212
790 1 0 $a Tamaki, Gertrud, $e advisor
790 1 0 $a Trost, Barry M., $e advisor
791 $a Ph.D.
792 $a 2006
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