Biselyngbyolide A (1) and B (2) exhibit cytotoxicity against several human cancer cell lines. They also induce apoptosis in mature osteoclasts. The structural elements of these macrolides are responsible for high affinities and unique binding modes with the substrates, however their exact mode of action/biological target remains unexplored. The presence of several (types) of double bonds, remote stereocenters enclosed in a macrolactone, lack of natural abundance and interesting bioactivities makes these compounds excellent synthetic targets. Our strategy for synthesis of these compounds is focused on rapid and short synthesis of C1-C13 fragment which would serve as a common intermediate for both compounds. Our convergent synthesis relies on catalyst controlled installation of stereocenters and minimum protecting group manipulations. Details of these studies will be presented.

Synthesis of the biselyngbyolides through rapid and convergent synthesis of C1–C13 fragment

253rd National Meeting (2017)

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