Aplysqualenol A, isolated from a Caribbean sea slug, Aplysia dactylomela, has demonstrated antitumor activity against SNB-19 CNS cancer and T-47D breast cancer in vitro along with viral activity against Herpes simplex types 1 and 2.  The use of procedural information from the previously synthesized molecule thyrsiferol has provided significant assistance in the synthesis of the alkynyl bromide (C8-C15) portion of the molecule.  Slight modifications were incorporated in order to account for a different stereocenter configuration at C14. Reactions chosen gave optimal yields for each of the synthetic steps.  After these yields were optimized, reactions were performed on a larger scale in order to push product through for later steps.

Progress towards synthesis of Aplysqualenol A

239th National Meeting (2010)

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