Total Syntheses of the Lycopodium Alkaloids Luciduline, Nankakurines A and B, Lyconadin C and the Aspidosperma Indole Alkaloid Subincanadine F PDF Download
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Author: Xiayun Cheng
Publisher:
ISBN:
Category :
Languages : en
Pages : 680
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Book Description
A total synthesis of the bridge-fused Aspidosperma indole alkaloid (±) has been accomplished in seven steps starting from the commercially available tryptamine. The bridge-containing scaffold of (±)-subincanadine F was efficiently assembled by a low valent titanium mediated intramolucular nucleophilic acyl substiutution (INAS) reaction. The synthetic utility of titanium-medicated INAS reagents for heterocyclic compounds was further demonstrated.
Author: Xiayun Cheng
Publisher:
ISBN:
Category :
Languages : en
Pages : 680
Get Book Here
Book Description
A total synthesis of the bridge-fused Aspidosperma indole alkaloid (±) has been accomplished in seven steps starting from the commercially available tryptamine. The bridge-containing scaffold of (±)-subincanadine F was efficiently assembled by a low valent titanium mediated intramolucular nucleophilic acyl substiutution (INAS) reaction. The synthetic utility of titanium-medicated INAS reagents for heterocyclic compounds was further demonstrated.
Author: Sarah Elizabeth House
Publisher:
ISBN:
Category :
Languages : en
Pages : 370
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Book Description
A unified approach to the total synthesis of Lycopodium alkaloids belonging to the miscellaneous class has been developed, wherein a single tetracyclic amine is employed as a common intermediate in synthetic studies toward several alkaloids. An overview of Lycopodium alkaloids is presented, including their structural classification, isolation and biological activity. The biosynthesis of alkaloids in the miscellaneous group is discussed in depth. A summary of previous synthetic work focusing on miscellaneous Lycopodium alkaloids is presented, including total syntheses of luciduline, lyconadins A and B and nankakurines A and B.A model study of spirolucidine is discussed. A biomimetic route to access spirolucidine and nankakurine B has been investigated. In this study, a tetracyclic amine that is a key intermedite in the total synthesis of lyconadin A previously developed in our laboratory is elaborated into a tertiary alcohol that mimics the proposed biosynthetic precursor of nankakurine B.A biomimetic ring-contractive [alpha]-hydroxyimine rearrangement to generate nankakurine B has been extensively investigated and found to be disfavored. The conversion of a tricyclic ketone (first synthesized en route to lyconadin A) to the tetracyclic core of serratezomine D has been investigated. The core of this molecule was inaccessible via methods employed in the studies toward lyconadin A. The total synthesis of 1'-epi-dihydrolycolucine from the key common tetracyclic amine intermediate has been achieved. Studies toward the synthesis of serratezomine E served as a platform to develop this method and to determine the stereochemical outcome of this reaction.
