Publisher Summary This chapter discusses the experimental approaches to antifungal chemotherapy. Fungal diseases in general occur in all parts of the world and affect all ages, though a number of particular species are restricted geographically in their incidence. It goes without saying that a systemic fungal infection will require systemic treatment. When however the fungus is confined to the skin or mucosal membranes, then the possibility exists of applying a topical treatment to the affected area, or alternatively treating the infection systemically, getting the parasite from “behind.” With a topical treatment the patient may feel he is doing something positive by applying the medication to the lesion whereas an oral treatment may give the feeling of irrelevance. On the other hand there would seem little point in applying a messy treatment to an already messy lesion if an alternative oral treatment were available.

Experimental approaches to antifungal chemotherapy.

Dormantinol, a possible precursor in solanidine biosynthesis, from budding Veratrum grandiflorum

A simple, efficient, and general α-prenylation approach for the synthesis of a variety of α-prenylated alcohols has been successfully developed. A wide range of α-prenylated alcohol derivatives could be obtained in good yields by highly α-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 °C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct α-prenylation of carbonyl compounds in a highly α-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.

General and highly α-regioselective zinc-mediated prenylation of aldehydes and ketones.

Guaianolides, heliangolides, diterpenes and cycloartenol derivatives from Balsamorhiza sagittata

A new lanostane type triterpene with a lactone partial structure in the side chain was isolated from the sclerotium of the wood rotting fungus Inonotus ob/iquus together with three known compounds; lanosterol, inotodiol and trametenolic acid. The new compound was determined to be 3 It-hydroxy8,24-dien-lanosta-21,23-lactone by spectroscopic analyses. Biogenesis of the new triterpene is proposed in relation to the compounds found in the fungus so far.

/pdf/chemical-constituents-of-inonotus-obliquus-i-a-new-2gi2ozdq7q.pdf

F. de Reinach Hirtzbach

Papers

The stereospecific synthesis of inotodiol 3β, 22R-dihydroxylanosta-8,24-diene

Stereospecific synthesis of inotodiol (3beta,22r-dihydroxylanosta-8,24-diene)