Total synthesis of Zoanthamine

University Of California San Diego, La Jolla CA

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Abstract

DESCRIPTION (provided by applicant): Our goal is to develop a feasible synthetic procedure that can yield Zoanthamine and other members of this alkaloid family such as norzoanthamine in a concise manner. Most of these alkaloids possess highly functionalized trans-decalone and heterocyclic aminal ring system along with at least three quaternary chiral centers (C-9, C-12, C-22 for zoanthamine). Zoanthamine and its relatives were found to inhibit phorbol myristate acetate induced inflammation in a model system. Norzoanthamine was found to inhibit the growth of P388 murine leukemia cell cultures. In addition, norzoanthamine inhibits IL-6 production. Recently, it has been reported that zoanthamine-type alkaloids suppress the decrease in bone weight. The construction of the core of zoanthamine will lead us to hopefully develop a library of its analogs to further study their potential as candidates for an osteoporotic drug and/or an anti-inflammatory drug.