Facile and efficient addition of terminal alkynes to benzotriazole esters: synthesis of D-ERYTHRO-SPHINGOSINE (cas 123-78-4) using ynones as the key intermediate

Add time:09/24/2019    Source:sciencedirect.com

From the perspective of synthesis, ynones are compounds of considerable interest because of their occurrence in a wide variety of biologically active molecules and as key synthetic intermediates. In this context, a facile and highly efficient synthesis of ynones was developed based on the high reactivity of benzotriazole esters formed in situ. Lithium acetylides can alkylate various carboxylic acids in yields ranging from 60% to 92%. To determine whether our methodology is useful for synthesising complex and biologically relevant molecules, we synthesise D-ERYTHRO-SPHINGOSINE (cas 123-78-4) in four steps and with 33% overall yield from l-serine.

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