Thiocladospolide A is a macrolactone first isolated in 2019 from the fungus <i>Cladosporium cladosporioides</i>. As with several sulfur-containing natural products, it was found to have antibacterial and anti-inflammatory properties. We have proposed a synthesis of this molecule based around a regioselective conjugate addition of a thiol group to patulolide B, whose structure matches the thiocladospolide macrolactone. In order to achieve this conjugate addition, two syntheses of patulolide B have been proposed. The first is a novel stereoselective synthesis, the second, a more rapid non-stereoselective synthesis beginning with readily available starting materials. Our results toward the synthesis of thiocladospolide A via both routes will be presented.

Efforts toward the synthesis of thiocladospolide A

ACS Spring 2022

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