Efforts Towards the Total Synthesis of Thiocladospolide A via Conjugate Addition to Patulolide B
Start Date
29-4-2022 2:15 PM
Location
Alter Hall Poster Session 1 - 2nd floor
Abstract
Thiocladospolide A is a natural product first isolated in 2019 from the fungus Cladosporium cladosporioides. Similar to many other sulfur-containing natural products, it was found to have anti-bacterial 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 macrolactone seen in thiocladospolide. In order to achieve this conjugate addition, two syntheses of patulolide B have been proposed as well. The first is a novel stereoselective synthesis that will yield the stereochemistry seen in thiocladospolide A when it was isolated. The second is a novel non-stereospecific synthesis beginning with an unsaturated fatty acid that yields a large amount of racemic patulolide B in fewer and simpler steps than the first synthesis. This synthesis was designed as a faster alternative that allows us to test the efficiency of the conjugate addition method before beginning the stereoselective process.
Efforts Towards the Total Synthesis of Thiocladospolide A via Conjugate Addition to Patulolide B
Alter Hall Poster Session 1 - 2nd floor
Thiocladospolide A is a natural product first isolated in 2019 from the fungus Cladosporium cladosporioides. Similar to many other sulfur-containing natural products, it was found to have anti-bacterial 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 macrolactone seen in thiocladospolide. In order to achieve this conjugate addition, two syntheses of patulolide B have been proposed as well. The first is a novel stereoselective synthesis that will yield the stereochemistry seen in thiocladospolide A when it was isolated. The second is a novel non-stereospecific synthesis beginning with an unsaturated fatty acid that yields a large amount of racemic patulolide B in fewer and simpler steps than the first synthesis. This synthesis was designed as a faster alternative that allows us to test the efficiency of the conjugate addition method before beginning the stereoselective process.
