Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow

A short total synthesis of ajoene, (E,Z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting ma...

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Detalles Bibliográficos
Autores principales: Raynbird, Marina Yamamoto, Silva, Filipa, Smallman, Harry, Khokhar, Shaista S., Neef, Daniel, Evans, Gareth J. S., Wirth, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384054/
https://www.ncbi.nlm.nih.gov/pubmed/32364668
http://dx.doi.org/10.1002/chem.202001598
Descripción
Sumario:A short total synthesis of ajoene, (E,Z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and disulfide formation/ allylation, the target product can be obtained at a rate of 0.26 g h(−1) in an overall yield of 12 %.

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