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
Year: 2020
Type: article
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 %.
Source: Chemistry - A European Journal
Authors: Marina Yamamoto Raynbird, Filipa Silva, Harry Smallman, Shaista S. Khokhar, Daniel Neef, Gareth J. S. Evans, Thomas Wirth
Institution: Cardiff University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,000
Funders: Bangor University, European Social Fund
OpenAlex ID: W3021862989