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An Approach to the Synthesis of Lycopodium Alkaloids

Author: Friedrich K. Hess
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 0

Book Description

An Approach to the Synthesis of Lycopodium Alkaloids

Author: Friedrich K. Hess
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 0

Book Description

An Approach to the Synthesis of Lycopodium Alkaloids

Author: George Alexander Cooke
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 0

Book Description
The compound N-acetyl-2-chloro-2-(3~aminopropyl)- cyclohexanone (LXXXI) has been prepared by the alkylation of the pyrrolidine enamine of cyclohexanone, followed by hydride reduction of the corresponding ethylene ketal, acetylation, hydrolysis of the ketal, and chlorination of the resulting N-acetyl ketone. In a more direct approach to a lycopodine system, a series of hexahydrojulolidine derivatives, oxygenated at C-9 and carrying a substituent at C-ll, were prepared. Thus Birch reduction of 9-methoxyjulolidine XXVIII yielded the dihydro-derivative XXXVI which on treatment with ethylene glycol and perchloric acid was converted to the ethylene-ketal iminium perchlorate XCVIII, This substance was then subjected to the conditions of the Grignard reaction using methallyl magnesium chloride (CVII) to produce the corresponding C-ll adduct as two stereoisomers CX (all trans) and CXI (all cis), the latter being the major product. Pure CXI was obtained by column chromatography and experiments were carried out to deter-* mine its stereochemistry. Treatment of the CXI (as its perchlorate) with ozone followed by catalytic reduction of the ozonide produced the ketone CXXIII and several attempts were made to convert this to the annotinine II skeleton by photochemical methods. Reactions were as well performed designed to introduce unsaturation at C-7a, 8 thus providing a compound which might be expected to produce the cis-trans isomer (CXLIV) on dissolving metal reduction> The mass spectra of several of these derivatives were measured and are interpreted by analogy with fragmentations observed in several Lycopodium alkaloids.

A Biogenetic Approach to the Synthesis of the Lycopodium Alkaloids

Author: Gregory Wayne Schwing
Publisher:
ISBN:
Category :
Languages : en
Pages : 140

Book Description

Lycopodium Alkaloids

Author: Jerold Steven Horn
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 150

Book Description

Approaches to the Total Synthesis of the Lycopodium Alkaloid Fawcettimine and Related Studies

Author: Todd Andrew Blumenkopf
Publisher:
ISBN:
Category :
Languages : en
Pages : 648

Book Description

Unified Approach to the Lycodine Lycopodium Alkaloids

Author: Michael David Purdham
Publisher:
ISBN:
Category :
Languages : en
Pages : 198

Book Description

A Unified Approach Toward the Total Synthesis of Lycopodium Alkaloids of the Miscellaneous Class

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.