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 easy 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
9); the second Scheme 9 Biosynthesis of Compounds Containing an Indole Nucleus 35 hypothesisZo7suggests a derivation of the ten carbons from the condensation of three acetate units, a malonate unit, and a C, unit (Eq. 10); the third postulateZoRargues for a C,-,, skeleton derived from prephenic acid in 209 proposes combination with a C, unit (Eq. 11); and the last suggestionZwb* the cleavage of a cyclopentane monoterpene skeleton to arrive at the required Cglo fragment (Eq. 12). Experimental work by Leete's group initially appeared to substantiate the 210* 211 Incorporation of sodium 14C-formate into second hypothesis,207* ajmaline (65) by RauwolJia serpentina reportedly gave the alkaloid bearing 12% of its activity at C-21.
Plieninger has synthesized 54 containing 14C and found176that it is incorporated into elymoclavine with modest efficiency. ~ 55 and compared its effectiveness as a precursor in competition with 54; the latter substance was always more efficiently utilized. 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 .
By the use of mass spectrometry, Scottzz7localized the deuterium in the vindoline generated in rico from 1-2H2geraniol which was presumed to be 75; ions (a), (b), and (c) each showed enrichment levels corresponding to the presence of one deuterium atom while ions (d) and (e) showed no enrichment, in agreement with expectation. The data obtained with labeled geraniol are readily accommodated by the processes of Scheme 12. With the efficacy of geraniol as an indole alkaloid precursor amply proven, attention was next turned to the known cyclopentanoid monoterpenes in the search for a likely candidate for the postulated ring-cleavage and rearrangements.