Pen-Chung Wang

Synthesis of Heterocyclic α-Amino Acids

Abstract Although there are several reported methods for the synthesis of amino acids,1–11 most of these require conditions which are unsuitable for sensitive precursors. An important exception is the route developed by Ugi and co-workers6–11 involving condensation of a carbonyl compound, carboxylic acid, amine, and isocyanide at temperatures ranging from -78° to 25° C.

Chapter 6 Muscarine Alkaloids

Publisher Summary The alkaloid muscarine is found in a variety of fungi along with choline, acetylcholine, and other basic physiologically active compounds. Included among these fungi are mushrooms of the very poisonous Amanita species: A. phalloides (death cap) and A. muscaria (fly agaric). The effects of nutritional factors on muscarine production of Clitocybe riuulosa surface cultures were studied. Combinations of mannitol or sorbitol with beer wort afforded the best muscarine production. The chemical classes of compounds found in mushrooms that affect the nervous system are (1) muscarine, (2) acetylcholine, (3) ibotenic acid and muscimol, and (4) psilocybinpsilocin. This chapter explores the natural occurrence of muscarine and stereoisomers and how to isolate them. Structural and conformational studies of muscarine are undertaken, along with synthetic investigations of muscarones and dehydromuscarones and synthetic investigations of muscarines and stereoisomers. Biological activity of muscarines, muscarones, their stereoisomers, and analogs are presented, along with structure-activity relationships in muscarine, its stereoisomers, and analogs.