Method for Synthesizing Novel Furanosteroids

The furanosteroids are a class of pentacyclic fungal metabolites that share in common a furan ring bridging positions 4 and 6 of the steroid skeleton. Members of this class are known for their powerful anti-inflammatory and antibiotic properties as well as their ability to selectively block certain intracellular signaling pathways, in particular those associated with cell growth and development. Accordingly, furanosteroids such as viridin and wortmannin have potential as therapeutic agents for diseases characterized by rapid cell proliferation, including cancer.

Dartmouth researchers have now found a novel method for synthesizing furanosteroids and related materials. The method involves directly transforming a functionalized alkyne oxazole to a furo[2,3-b]phenol derivative by an intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization; and elaborating the furo[2,3-b]phenol derivative by intermolecular and intramolecular aldol ring closing condensations. Given that viridin and wortmannin are attractive lead structures for designing selective inhibitors of both PI3K and Polo-like kinase (PLK1), this synthetic method finds application in synthesizing novel and more efficacious structural analogs.

This technology is claimed in a pending patent application. We are seeking an industrial partner interested in its commercialization. (Ref:J373

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