Stachybotrin D is a novel phenylspirodrimane isolated from <i>Stracybotrys Chartarum</i> <i>MXH-X73</i>. Stachybotrin D exhibits anti-HIV properties by acting as a non-nucleoside reverse transcriptase inhibitor (NNRTI) on wild type HIV-1 and 5 NNRTI resistant strands. The structure of Stachybotrin D is distinct from the other available NNRTI drugs, and is a potential new chemotype for NNRTI drug treatments. Our research group has developed a synthetic method towards a total synthesis of Stachybotrin D. The retrosynthetic analysis developed incorporates synthesized phenyl and sesquiterpene moieties which are assembled together through a furan ring. We will discuss our efforts towards this synthesis, with a focus on utilizing greener chemistry methods. This includes using a Vilsmeier-Haack reaction as a milder condition rather than a Gatterman reaction which uses hydrogen cyanide for a formylation step. Additionally, we utilize a microwave reactor for some of the steps rather than exhaustive heating to reduce the energy usage and time. The paper presented demonstrates the strategy taken by our group and the current work towards this synthesis.

Methods towards the synthesis of Stachybotrin D

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.