137379-04-5Relevant articles and documents
Facile and efficient addition of terminal alkynes to benzotriazole esters: Synthesis of d-erythro-sphingosine using ynones as the key intermediate
Morales-Serna, José Antonio,Sauza, Alejandro,Padrón De Jesús, Gabriela,Gavi?o, Rubén,García De La Mora, Gustavo,Cárdenas, Jorge
supporting information, p. 7111 - 7114 (2013/12/04)
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 in four steps and with 33% overall yield from l-serine.
