76361-77-8Relevant articles and documents
A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity
Alonso, Isabella G.,Yamane, Lais T.,de Freitas-Blanco, Ver?nica S.,Novaes, Luiz F.T.,Franz-Montan, Michelle,de Paula, Eneida,Rodrigues, Marili V.N.,Rodrigues, Rodney A.F.,Pastre, Julio C.
, p. 5192 - 5199 (2018/07/06)
A 5-step synthesis of spilanthol (affinin) is reported, where the route features complete control of alkene geometry during the assembling of the double bonds, with the use of a Sonogashira cross-coupling reaction, a Z-selective alkyne semi-reduction and a HWE olefination reaction as the key steps. A simplified analogue was also prepared in 4 steps. Both compounds were found to permeate dermatomed pig ear skin through an in vitro Franz-type diffusion cell. The simplified analogue presented a superior anesthetic effect in vivo, using the tail flick model, when compared to spilanthol and to the commercial standard EMLA. These results suggest that both spilanthol and its analogue could be useful as a topical anesthetic in clinical practice.
Efficient Preparation of Functionalized (E,Z) Dienes Using Acetylene as the Building Block
Wang, Zhong,Lu, Xiyan,Lei, Aiwen,Zhang, Zhaoguo
, p. 3806 - 3807 (2007/10/03)
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FACILE R0UTES TO NATURAL ACYCLIC POLIENES. SYNTHESES OF SPILANTHOL AND TRAIL PHEROMONE FOR TERMITE
Ikeda, Yoshihiko,Ukai, Junzo,Ikeda, Nobuo,Yamamoto, Hisashi
, p. 5177 - 5180 (2007/10/02)
The synthetic procedures for spilanthol and trail-following pheromone for a southern subterranean termite were described.The syntheses heavily depend on the new diene synthesis using titanium reagent.
