Vivus, Inc.

Pharmatech International, Inc.

Heterocyclic Research, Inc.

Miroslav Trampota

Matthew Pincus

Bohumil Zak

This invention relates to a novel process for the preparation of optically pure L-(+)-ergothioneine. The process for the chemical synthesis of L-ergothioneine comprises steps which consist of reacting L-histidine alkyl ester with an acid halide, chloroformate or pyrocarbonate in the presence of a base, hydrolysis of the alkyl-(S,Z)-2,4,5-triamidopent-4-enoate to obtain a (S)-alkyl 2,5-diamido-4-oxopentanoate, acid catalyzed hydrolysis of the (S)-alkyl 2,5-diamido-4-oxopentanoate followed by reaction with a metal thiocyanate to obtain the thiohistidine, protection of the sulfur of thiohistidine as the tert-butyl thioether, dialkylation of the primary amine to obtain a tertiary amine, quaternization of the tertiary amine, and removal of the protecting group to obtain the desired (S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trialkylammonio)propanoate (I). This process affords a better yield and is capable of practical application at large scale.

Process for the synthesis of L-(+)-ergothioneine

A process for synthesizing prostaglandin E.sub.1, E.sub.2 and derivatives thereof is provided. The process is a 'one-pot' method in which 2-furyllithium, copper cyanide, a lower alkyllithium reagent and either an (E)-alkenylstannane or a halogenide are combined with cyclopentenone (II) ##STR1## in which A, R.sup.6 and R.sup.7 are as defined herein. The reaction gives rise to the desired prostaglandin product in yields of 80% or higher.

Process for preparing prostaglandin E1, E2 and analogs thereof using

Synthetic linear or cyclic peptides having the formula

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West Orange, NJ, United States of America

Miroslav Trampota