Total synthesis of the falcarinol-type oxylipin (3S)-16,17-didehydrofalcarinol and its activity against Leishmania mexicana
2022
Larqué, Horacio | Carrillo-Aké, Ana G. | de la Vega, Jennifer | Peraza-Sánchez, Sergio R. | Carballo, Rubén M. | Chávez-Montes, Abelardo | del Olmo, Esther
This paper reports a novel synthesis route to obtain (3S)-16,17-didehydrofalcarinol (1a) in order to provide the quantities necessary for in vivo tests. For this purpose, a two-synthon coupling synthesis was applied. On the one hand, the (Z)-10-bromodeca-1,8-diene (10) was obtained throughout nine steps, and on the other, the hepta-1-en-4,6-diyn-3-ol (11) was obtained in one single step, the fragments were coupled to give the racemic 1 in 27% yield. Finally, chiral chromatography resolution of 1 provided the desired enantiomer 1a (27 mg), which was tested against Leishmania mexicana, demonstrating its high and effective bioactivity (IC₅₀ = 0.74 μM).
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