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Towards the Synthesis of Polysulfurous Molecules Found in Shiitake Mushrooms (Lentinula Edodes) and Optimizing the Synthesis of Allenyl Sulfoxides from Thiosuccinimides

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Title: Towards the Synthesis of Polysulfurous Molecules Found in Shiitake Mushrooms (Lentinula Edodes) and Optimizing the Synthesis of Allenyl Sulfoxides from Thiosuccinimides
Author: Riddell, Adam
Department: Department of Chemistry
Program: Chemistry
Advisor: Schwan, Adrian
Abstract: First project - Lentinic acid, the precursor to lenthionine (the primary aroma producing compound of shiitake mushrooms), represents a valuable synthesis target due its natural isomer being unknown and the lack of literature about the final non-enzymatic step of its conversion to lenthionine. The synthesis of lentinic acid provides an opportunity to explore novel organosulfur chemistry as it contains a previously unreported sulfur carbon. The primary focus of this research was to investigate the synthesis of lentinic acid via novel organosulfur methods. The first objective was the synthesis of β-sulfonyl sulfinate esters/sulfinamides from sulfones. The second objective was the investigation of the double deprotonation chemistry of β-bis-sulfoxides with the goal of reacting them with the β-sulfonyl sulfinate esters/sulfinamides to synthesize lentinic acid. The final objective was the synthesis of lentinic acid via an iterative sulfenate release. These objectives were unsuccessful and alternative methods should be investigated for the synthesis of lentinic acid. Second project - Due to their value in natural product synthesis and potential in stereoselective reactions, allenes are of great interest. Investigation in the Schwan group has focused on the synthesis of allenyl sulfoxides, but no universally optimized method for this purpose had been found. The focus of this research was the optimization of work performed by previous Schwan group members for the synthesis of allenyl sulfoxides from thiosuccinimides via a [2,3]-sigmatropic rearrangement. The primary objective was optimizing the yields of various allenyl sulfoxides by varying the reaction temperature and basic conditions of the reaction between thiosuccinimides and propargyl alcohols. The secondary objective was the synthesis of various allenyl sulfoxides utilizing the optimized conditions. The use of chloroform and K₂CO₃ at 50 °C was determined to be the optimal conditions for the synthesis of most allenyl sulfoxides and these conditions were utilized for the synthesis of 20 allenyl sulfoxides from thiosuccinimides.
URI: https://hdl.handle.net/10214/25488
Date: 2021-04
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