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Short Paper | Regular issue | Vol 100, No. 10, 2020, pp.1623-1632
Published online, 27th August, 2020
DOI: 10.3987/COM-20-14288
■ Design and Synthesis of Pentacycloundecane Cage Compound Containing Oxazole Moiety

Sambasivarao Kotha* and Subba Rao Cheekatla

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India

Abstract

Here, we have established a new and simple synthetic approach to the pentacycloundecane containing cage oxazole unit in four steps. The synthesis begun with a cheap and readily available materials such as 2,5-dimethoxybenzaldehyde and endo-dicyclopentadiene. This approach relies on Van Leusen oxazole synthesis and [2+2] photocycloaddition as key steps. To the best of our knowledge, this is the first example of Cookson’s dione containing oxazole ring system. Some of these oxazole motifs are useful in bioorganic chemistry and our results are likely to draw the attention of medicinal chemists