The synthesis of a methylene bridged cavitand with functionalized bromobenzene feet is described. A microwave reaction was explored as an alternative to the traditional resorcinarene synthesis, resulting in a reduction in reaction time from seven days to five minutes and resulted in a 17% crude yield. Additionally, a pressure vessel was used for the bridging reaction to complete the cavitand synthesis. The pressure vessel was found to reduce the reaction time from ten days to four hours and resulted in a 53% crude yield. The resulting cavitand can be thiolized through lithium halogen exchange to yield a thiophenol footed cavitand. These octathiol cavitands can then be coupled to peptides to generate template assembled synthetic proteins for use in protein design and protein folding studies.

Synthesis of a cavitand for use in eight-helix template assembled synthetic protein systems

255th National Meeting (2018)

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