Stachybotrin D is a secondary metabolite derived from a sponge fungus. It is a non-nucleoside reverse transcriptase inhibitor of wild type HIV-1 and 5 NNRTI resistant strands. For this reason, Stachybotrin D which is in the phenylspirodrimane family has received attention in our research group.  The approach to the natural product used a convergent synthesis strategy, where we break structure into three components: a phenyl backbone containing a cyclic amide, a diterpenoid derivative in which a furanyl ring added to the phenolic component and incorporation of the stereochemistry. The work presented here will focus on the addition of a bicyclic component via a of the structure. Other group members focused on the synthesis of the other components of the synthesis strategy. In addition to the synthesis of the fragments, an aim in our group is greener synthetic strategies especially those that could later even be utilized in teaching laboratories. This retrosynthesis incorporates a modified Grignard and protecting steps which were modified to incorporate greener synthesis methods. The study will compare the original methods to modified methodologies that include microwave synthesis and macro reticular polystyrene based ion exchange resins.<br/>

Towards the synthesis of Stachybotrin D

253rd National Meeting (2017)

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