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Chemistry of Heterocyclic Compounds: Indoles, Part Two, by William J. Houlihan

By William J. Houlihan

Content material:
Chapter III Biosynthesis of Compounds Containing an Indole Nucleus (pages 1–64): Ronald J. Parry
Chapter IV Alkyl, Alkenyl and Alkynyl Indoles (pages 65–126): Dr. Lowell R. Smith
Chapter V Haloindoles and Organometallic Derivatives of Indoles (pages 127–178): James C. Powers
Chapter VI Chemistry of Indoles wearing uncomplicated capabilities (pages 179–537): F. Troxler
Chapter VII Oxidized Nitrogen Derivatives of Indole and Indoline (pages 539–605): Kent Rush

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Extra resources for Chemistry of Heterocyclic Compounds: Indoles, Part Two, Volume 25

Sample text

Evidence against the generation of the C,-,, unit by Woodward fission comes from Battersby’s The two ipecac alkaloids, cephaeline (69) and emetine (70), contain a Corynanthe-type skeleton, but condensed with a phenethylamine residue rather than with tryptamine; conclusions derived from tracer studies on the ipecac alkaloids may therefore be applied, with some reservations, to the indole alkaloids. A) was supplied to Cephaelis ipecacuanha, radioactive cephaeline was produced which was specifically labeled at C-3 and C-3’, but not at (2-1’; hence, 3,4-dihydroxyphenylalanine is not a likely precursor for the C,-,, unit of these alkaloids.

Biosynthetically labeled elymoclavine was converted chemically into chanoclavine-I bearing greater than 90% of its activity in the hydroxymethylene carbon. The incorporation of this substance gave labeled agroclavine, shown by degradation to carry over 96 % of the activity at C-7. The conversion of chanoclavine-I into agroclavine must therefore be accompanied by a trans to cis isomerization of the 8,9-double-bond. Experiments under similar conditions with hydroxymethylene labeled isochanoclavine-I failed to disclose any significant incorporation of the compound into the tetracyclic ergolines.

More recently, Plieninger's group synthesized 54 labeled with I4Cat C-1 of the ally1 side-chain and with 3H at C-2' of the alanine sidechain; the doubly-labeled substance was incorporated into agroclavine and elymoclavine without a change in the 3H/14Cratio, indicating an intact utilization of the c o m p ~ u n d . ~14C-4-(y,y-DimethylaIlyl)tryptamine ~z was by contrast only poorly incorporated into the clavine alkaloids, and in fact served as an inhibitor of alkaloid formation. This result speaks in favor of isoprenylation occurring before the decarboxylation and N-methylation processes, a conclusion that harmonizes with other experimental evi~ ~ found 54 in a d e n ~ e .

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