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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.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Transition metal-catalyzed reactions of alkynes: Investigation of Mannich-type addition reactions and studies on the total synthesis of (+)-streptazolin and (-)-laulimalide.
作者:
Chung, Cheol Keun.
面頁冊數:
369 p.
附註:
Advisers: Barry M. Trost; Gertrud Tamaki.
附註:
Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2552.
Contained By:
Dissertation Abstracts International67-05B.
標題:
Chemistry, Organic.
電子資源:
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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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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369 p.
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Advisers: Barry M. Trost; Gertrud Tamaki.
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Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2552.
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Thesis (Ph.D.)--Stanford University, 2006.
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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.
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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.
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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.
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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.
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