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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

Raynbird, Marina Yamamoto, Silva, Filipa, Smallman, Harry, Khokhar, Shaista S., Neef, Daniel, Evans, Gareth J. S. and Wirth, Thomas 2020. 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. Chemistry - A European Journal 26 (38) , pp. 8363-8367. 10.1002/chem.202001598

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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 %.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 0947-6539
Funders: KESS 2 program
Date of First Compliant Deposit: 24 June 2020
Date of Acceptance: 4 May 2020
Last Modified: 02 Sep 2020 15:43
URI: http://orca.cf.ac.uk/id/eprint/132777

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