Cover Feature: 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 (Chem. Eur. J. 38/2020). Issue 38 (17th 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: 8316
• Page End: 8316
• Publication Date: 2020-06-17
• Subjects: ajoene -- disulfides -- flow chemistry -- garlic -- organosulfur compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202002760
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract : Garlic, Allium Sativum, is native to Central Asia and is grown in China in extraordinary amounts, accounting for 80 % of the world's total production. Famous for its pungent odor and characteristic flavor, beneath its cloves are natural products with well‐known biological properties. There is still a distinct lack of reported total syntheses of its low molecular weight natural products, which are volatile and contain reactive moieties such as disulfides. In this work, the second chemical total synthesis of ajoene, an anti‐thrombotic agent, was developed in batch mode. Flow chemistry has also been developed to enable the synthesis of a novel sulfide without purification steps. More information can be found in the Communication by T. Wirth et al. on page 8363 .