Structural and Synthetic Studies on Some Lycopodium Alkaloids PDF Download
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Author: John Kenneth Jenkins Publisher: ISBN: Category : Alkaloids Languages : en Pages : 0
Book Description
Cernuine and the minor alkaloids, from Lycopodium cernuum, have been reexamined. The structure and stereochemistry of cernuine (I), CH 3 has been determined. The biosynthesis of cernuine is discussed. Some simple chemical transformations of annopodine have been carried out and are interpreted in light of its structure (II) as determined by 3 H II X-ray diffraction studies. Possible biosynthetic routes leading to annopodine are proposed. The synthesis of luciduline, an alkaloid from Lycopodium lucidulum, has been attempted.
Author: John Kenneth Jenkins Publisher: ISBN: Category : Alkaloids Languages : en Pages : 0
Book Description
Cernuine and the minor alkaloids, from Lycopodium cernuum, have been reexamined. The structure and stereochemistry of cernuine (I), CH 3 has been determined. The biosynthesis of cernuine is discussed. Some simple chemical transformations of annopodine have been carried out and are interpreted in light of its structure (II) as determined by 3 H II X-ray diffraction studies. Possible biosynthetic routes leading to annopodine are proposed. The synthesis of luciduline, an alkaloid from Lycopodium lucidulum, has been attempted.
Author: Kenneth Piers Publisher: ISBN: Category : Alkaloids Languages : en Pages : 0
Book Description
The transformation of lycopodine into annofoline via an unsaturated amido acetate has been carried out. This transformation is of biogenetic interest since lycopodine has been postulated to be the central intermediate in the biosynthesis of the Lycopodium alkaloids. The transformation of the unsaturated amido acetate obtained above into lycopodine has been carried out. This transformation is of potential use in the total synthesis of lycopodine since it provides a synthetic method of controlling the stereochemistry of the C-15 methyl group. The total synthesis of the cernuine ring skeleton has been achieved thus confirming the structural assignment made for the alkaloids cernuine and lycocernuine. The total synthesis was also useful in confirming the stereochemistry of the naturally occuring compounds .
Author: William Russell Bowman Publisher: ISBN: Category : Alkaloids Languages : en Pages : 0
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.
Author: Sarah Elizabeth House Publisher: ISBN: Category : Languages : en Pages : 370
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: Arnold Clifford Soper Publisher: ISBN: Category : Alkaloids Languages : en Pages : 0
Book Description
Original samples of some Lycopodium alkaloids isolated by Manske and Marion were examined. L.9 was found to be a molecular complex made up of the known alkaloid lycopodine (2) and of O-acetyllofoline (80). [Scientific diagrams] Studies related to the synthesis of lycopodine type alkaloids were carried out. Initially julolidine (15) was used as a model compound. Its reduction to an immonium salt was carried out and addition to C[subscript 11] of the immonium salt was found to proceed readily. The substitution products were found to have cis-cis ring junctures (e.g. 102). [Scientific diagrams] The synthetic study was extended to a more suitable system, 9-methoxyjulolidine (110). Reduction of this system followed by substitution at C[subscript 11] resulted mainly in cis - cis ring junctions in the products (e.g., 115). A method of changing the stereochemistry of the products from cis-cis to the synthetically useful cis - trans system was developed. A method for the formation of the fourth ring (D) inlycopodine type alkaloids was investigated. The method considered involved an internal aldol condensation in compound 152 to give 154. It was found that compound 152 could not be prepared at all readily, either by oxidation of 146 or by other methods investigated.
Author: Hans-Joachim Knoelker Publisher: Springer Science & Business Media ISBN: 3642255280 Category : Science Languages : en Pages : 268
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: John Kenneth Jenkins
Author: John Kenneth Jenkins
Author: Kenneth Piers
Author: Michael D. Curcumelli-Rodostamo
Author: William Russell Bowman
Author: Michaela C. Vertorano
Author: Todd Andrew Blumenkopf
Author: Sarah Elizabeth House
Author: Arnold Clifford Soper
Author: Aimin Wang
Author: Hans-Joachim Knoelker