Title: Towards the total synthesis of providencin
Language: English
Authors: Steinacher, Michael 
Qualification level: Diploma
Advisor: Enev, Valentin 
Issue Date: 2019
Number of Pages: 78
Qualification level: Diploma
Providencin is a highly oxygenated diterpenoid found in the sea plume Antillogorgia Kallos. It features a previously undescribed bicyclo[12.2.0]undecane carbon skeleton containing a tetrasubstituted cyclobutane ring, two trans-fused epoxides and a butenolide moiety. The absolute configuration of providencin remains to be proven. Biological testing revealed modest cytotoxic activity against several human cancer cell lines. This work presents the synthesis of an important building block en route to providencin based on a new retrosynthetic approach. Key steps are an enantioselective Lewis acid-catalyzed cycloaddition reaction to form the cyclobutane ring, a copper-assisted Stille-coupling under very mild conditions and the regioselective deprotection of just one of two trityl protecting groups.
Keywords: total synthesis; providencin
URI: https://resolver.obvsg.at/urn:nbn:at:at-ubtuw:1-122704
Library ID: AC15332099
Organisation: E163 - Institut für Angewandte Synthesechemie 
Publication Type: Thesis
Appears in Collections:Thesis

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