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. Issue 38 (15th June 2020)

• Record Type: Journal Article
• Authors: Raynbird, Marina Yamamoto; Silva, Filipa; Smallman, Harry; Khokhar, Shaista S.; Neef, Daniel; Evans, Gareth J. S.; Wirth, Thomas
• Is Part Of: Chemistry. Volume 26:Issue 38(2020)
• Page Start: 8363
• Page End: 8367
• Publication Date: 2020-06-15
• Subjects: ajoene -- disulfides -- flow chemistry -- garlic -- organosulfur compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001598
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 %. Abstract : Get into the flow ! A continuous flow synthesis of a novel sulfide is reported over four steps and has been biologically evaluated. In addition, a novel synthesis of ajoene has been established (see figure).