Green modifications to the Hajos pathway to the Wieland-Miescher ketone where investigated. Special emphasis was given to the second step, synthesis of the alcohol, and third step, synthesis of the enone product, with goals of increasing stereoselectivity in hot pressurized water. Given the hydrophilic nature of proline, more hydrophobic amino acids were tested. Lastly, to mimic the secondary amine properties of proline, N-boc Isoleucine was evaluated. Both changes lead to significant increases in stereoselectivity and overall yields of alcohol and enone mixed products.

Green modifications to the Hajos pathway to an important steroid intermediate

255th National Meeting (2018)

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