Approaches to the Total Synthesis of the Lycopodium Alkaloid Fawcettimine and Related Studies PDF Download
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Author: Todd Andrew Blumenkopf
Publisher:
ISBN:
Category :
Languages : en
Pages : 648
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Author: Todd Andrew Blumenkopf
Publisher:
ISBN:
Category :
Languages : en
Pages : 648
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Book Description
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.
Author: Damian Winston Young
Publisher:
ISBN:
Category :
Languages : en
Pages : 193
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Keywords: heterocycles, spirolucidine, alkaloids, dihydropyridones.
Author: Michael David Purdham
Publisher:
ISBN:
Category :
Languages : en
Pages : 198
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Author: Kathleen Tucker Hug
Publisher:
ISBN:
Category :
Languages : en
Pages : 340
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Author: Edward Fox Kleinman
Publisher:
ISBN:
Category :
Languages : en
Pages : 350
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Author: Hans-Joachim Knoelker
Publisher: Springer Science & Business Media
ISBN: 3642255280
Category : Science
Languages : en
Pages : 268
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Book Description
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-
Author:
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Category :
Languages : en
Pages :
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Spirolucidine is a complex alkaloid isolated from the club moss Lycopodium lucidulum. A three fragment convergent plan for the title compound was envisioned, with each fragment being derived from a chiral N-acyl-2,3-dihydro-4-pyridone. The synthesis of the bicyclic enecarbamate referred to as zone C was investigated. The first effort centered on a tandem intramolecular Diels-Alder reaction/retro Mannich ring opening reaction to set the key stereogenic centers within zone C.A second strategy aimed to ring open the tricyclic adduct which arises from the Diels-Alder reaction through an E1cB mechanism. Finally, a third attempt was made to utilize chirality transfer as a means to implement the necessary stereochemical elements of the bicyclic scaffold. The convergent union of the key fragments of spirolucidine was modeled on a simple substrate. The directed lithiation of N-Boc-dihydropyridines was utilized to prepare model 2,5,6-trisubstituted dihydropyridones of a general type needed for the completion of the spirolucidine synthesis.
Author: Barnett Bernstein
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 184
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Author: William Russell Bowman
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 0
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Book Description
The structure of the Lycopodium alkaloid lycofawcine (base L)(74) isolated by R. H. Burnell has been determined by the use of mass spectral analysis. The proposed structure was confirmed by transformation of lycofawcine into O-acetylacrifoline. The total synthesis of lycodine (6) was attempted but was not brought to a successful conclusion. The total synthesis of dl-lycopodine (1) has been achieved via a natural relay compound. A method for transforming 11-substituted cis - cis -hexahydrojulolidines (A) into the corresponding cis - trans -hexahydrojulolidines (B) has been developed.
