The intent of this research was to synthesize the isoindolinone moiety of Stachybotrin D, a phenylspirodrimane extracted from <i>Stachybotrys chartarum </i>MXH-X73, while incorporating Green Chemistry principles. This phenylspirodrimane was found to inhibit the reverse transcription activity of wild type HIV-1 as well as five other non-nucleoside reverse transcriptase inhibitor-resistant HIV strains. Due to the compound’s complexity, the synthesis of Stachybotrin D’s bicyclic moiety and phenyl backbone is being conducted by other research members. This synthesis involved the esterification of a benzoic acid derivative, protection of aromatic hydroxyl groups, and Mannich/Lactamization aminoalkylations. In the initial part of the project, Green Chemistry was applied towards performing esterification of various benzoic acid derivatives using a microwave reactor. Successful esterifications resulted in 85-94% yields. By developing a successful and greener synthesis of Stachybotrin D larger quantities of this natural metabolite may be produced for further study into its biological activity. Additionally, this research may advance current research into solving issues such as antibiotic resistance crisis and drug shortages.

Synthesis of the isoindolinone moiety of stachybotrin D: Incorporating greener methods

255th National Meeting (2018)

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