Indole Alkaloids. An Introduction to the Enamine Chemistry by W. I. Taylor

By W. I. Taylor

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Extra info for Indole Alkaloids. An Introduction to the Enamine Chemistry of Natural Products

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Bischler-Napieralski Condensation i//-3-€pialloyohimbanc 26 INDOLE ALKALOIDS 3. Acid catalysed equilibration of certain yohimbane derivatives at C-3 is mediated by one or more of the following equilibria the driving force being toward the direction of greater thermodynamic stability. Η c -Η" Η Η" 4. Autoöxidation products and their transformation products are well known for Type II and III alkaloids. 5. o '"==^N=^R, hydroperoxyindolenine R2 oxindole hydroxyindolenine pseudoindoxyl ö-acylaminoacylbenzene 4-quinolinoI 5.

This base, readily accessible via a Mannich condensation between indole, formaldehyde and dimethylamine, is produced in the plant from tryptophan by a route not completely understood but which retains the original indole moiety and the first carbon of the side chain. The usefulness of gramine to the plant is obscure but is certainly functional since in sprouting barley its concentration builds u p to a maximum in ten days after germination and has practically disappeared in a month. The most important indole in this molecule weight range is of course the auxin, indole-3-acetic acid.

2 are sketched some of the reactions whose interpreta­ tion lead to the deduction of the structures of the three bases. The work was not as simple as it is made to appear and for example the nature of the base (harman) which was originally produced by " o x i d a t i o n " of tryptophan with ferric chloride was obscure until the harmala alkaloids were investigated seventeen years later and the recognition of its structure was the key to this natural products problem. This pioneering work provided a solid basis for the later development of the chemistry of the yohimbines.

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