Organic solvent accounts for approximately 80% of hazardous waste generated in the pharmaceutical industry. This reality underscores the necessity of finding alternatives to organic solvent as reaction media. Water is an excellent alternative, as it is abundant, non-toxic, and non-hazardous. Unfortunately, water is often unsuitable because many organic reactants and reagents are water-insoluble. Aqueous micellar solutions can help mitigate the insolubility challenges, as water-insoluble starting materials and reagents are entropically driven into the hydrophobic micelle interior, which can facilitate organic reactions. Micelles have not only been shown to catalyze organic reactions, but often do so more efficiently, with fewer side-products, and at ambient temperatures. We are designing and synthesizing novel surfactants that self-aggregate into micelles capable of reversibly immobilizing starting materials or catalysts within the micelle. We report success on the synthesis of an alkene-terminating steroidal-PEG surfactant synthesized from lithocholic acid with a 50% yield in 5 steps. This synthesis was accomplished through an oxidation-decarboxylation pathway followed by PEG headgroup installation through the Fischer esterification pathway. We also report the progress of a more efficient and green synthetic route from lithocholic acid in only 3 steps involving the addition of allyl alcohol to the carboxylic acid of lithocholic acid to introduce the alkene. This approach removes the need for the protecting group strategy and use of lead(IV) tetraacetate used in our original synthesis.

Synthesis of alkene-terminating steroidal surfactants designed for micelle-catalyzed organic synthesis

255th National Meeting (2018)

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