Diversity-Oriented Synthesis of a Library of Podocarpic Acid Derivatives

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Avariety of compounds, with a related structure to podocarpic acid, have been found to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, insect toxicity and antifungal properties. In the present study, a series of synthetic derivatives of podocarpic acid have been prepared by chemical synthesis for potential biological evaluation as useful compounds for use in medicine and agriculture.

Podocarpic acid was first isolated from the resin of Podocarpus cupressins, an important timber tree which is endemic to Java, and later from Podocarpus dacrydioides ("Kahikatea") and Dacrydium cupressinum ("Rimu"), trees which are found in the timber regions of New Zealand. Since 1968, more than forty oxygenated metabolites of podocarpic acid have been isolated from various species of Podocarpus. Interest in these naturally occurring and synthetic lactones, podolactones, and related podocarpic acid derivatives has been mainly due to the novel structures of these compounds and the various types of biological activity possessed by them. Octahydrophenanthrene lactones and related podocarpic acid derivatives 3 have been reported to possess hormonal and anti-inflammatory properties. Other similar podolactones have been shown to inhibit the expansion and division of plant cells  to have antileukemic activity to have antibacterial activity to have insect toxicity properties and to exhibit antitumor activity.

Otherreports have indicated that these types of compounds, as a class, possess significant antifungal properties. The lactone 6 (Figure1), first isolated as a mold metabolite, was found to have significant activity against a number of fungi. The momilactones A 7 and B 8 have been shown to be fungitoxic towards Cladosporium cucumerinum. In a recent report several oxidized resin acid.