Search

Ajoene is a compound found in garlic extracts exhibiting a large range of biological activity. Novel ajoene analogues have been prepared in the search of compounds with superior bioactivity. Modifications include the alteration of the sulfoxide, the central alkene and the terminal allyl groups. [ABSTRACT FROM AUTHOR]

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 FROM AUTHOR]

Keywords: ajoene; biologic activity; disulfides; garlic; organosulfur compounds EN ajoene biologic activity disulfides garlic organosulfur compounds 1 1 1 02/12/21 20210210 NES 210210 B Garlic ( I Allium sativum i ) has a long history b as a food ingredient and traditional medicine, and garlic extracts have been known for a very long time to exhibit a wide range of biological properties (some general structures of ajoene analogues are shown on the picture of the plant). In their Full Paper on page 3008, Wirth et al. describe the synthesis of three non-natural I Allium i analogues. Ajoene, biologic activity, disulfides, garlic, organosulfur compounds. [Extracted from the article]

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) Keywords: ajoene; disulfides; flow chemistry; garlic; organosulfur compounds EN ajoene disulfides flow chemistry garlic organosulfur compounds 8316 8316 1 07/10/20 20200708 NES 200708 B Garlic, Allium Sativum b , is native to Central Asia and is grown in China in extraordinary amounts, accounting for 80 % of the world's total production. Ajoene, disulfides, flow chemistry, garlic, organosulfur compounds. [Extracted from the article]