By William J. Houlihan
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 sporting 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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Additional info for Chemistry of Heterocyclic Compounds: Indoles, Part Two, Volume 25
The loss of some of the 4R-hydrogens was ascribed to an isotope effect in a subsequent stage of the biosynthesis. 199It is therefore a reasonably safe assumption that the over-all stereochemistry of the reaction is also the same as in these systems; this assumption predicts that the label from C-2 of mevalonic lactone should be located in the trans methyl group of the original dimethylallyl moiety. Thus, two isomerizations of the allylic double-bond apparently occur in the formation of the tetracyclic ergolines.
The structures of the three isomeric chanoclavine alkaloids, chanoclavine-I (53), chanoclavine-I1 (56), and isochanoclavine-I (57), are shown here; the absolute configuration 56 57 of chanoclavine-I at C-5 and C-10 was determined by Hofmann's group191by correlation with festuclavine, while the configurations of the other two alkaloids are due to Stauffacher and T ~ c h e r t e r The . ~ ~ ~stereochemistry assigned to chanoclavine-I and isochanoclavine-I was recently confirmed by Arigoni et Biosynthesis of Compounds Containing an Indole Nucleus 31 Though it is not yet certain whether chanoclavine-I is an obligatory intermediate in ergot alkaloid biosynthesis, the ability of the base to serve as an efficient precursor of the tetracyclic ergolines has been amply demonstrated; the incorporation levels into agroclavine, elymoclavine, and lysergic acid amide in C.
Administration of methyl-3H-~~-methionine to R . serpentina procured additional evidence against incorporation of a C, unit; the resulting ajmaline carried 97% of its total activity in the N-methyl group. lI6 The data amassed in the testing of the acetate hypothesis not only speaks heavily against an acetate origin for the ubiquitous CB-lounit, but also casts CHaO H CHaOOC 68 22 67 a shadow of doubt across the other two hypotheses that require the specific incorporation of a C , unit. Relevant data supporting this doubt was soon forthcoming.
Chemistry of Heterocyclic Compounds: Indoles, Part Two, Volume 25 by William J. Houlihan