Short Total Synthesis of Ajoene

Abstract

We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

Synthesis of Ajoene Analogues by Novel Synthetic Strategies

“…In 2018, we reported the first total synthesis of 3 (Scheme 1 c). The chemical total synthesis overcame obstacles such as the instability and volatility of 2 by replacing allicin with alternative starting materials to develop a reliable and robust five step synthesis [3] . More recently, the precursor 4 was synthesized in a flow process and also converted to 3 (Scheme 1 d).…”

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

“…These products provide odour and some therapeutic benefits to these herbs, and consequently are important materials in F&F and pharmaceutical industry [360]. Different procedures for their synthesis have been disclosed so far and sulfide oxidation is described as the key step (Scheme 93) [361][362][363][364]. For instance, ajoene (386) can be prepared by hydrolysis and sulfenylation of the thioenaloate starting material 384 to prepare the intermediate 385, which can then be oxidised to the desired material 386.…”

Garlic extract in prosthesis-related infections: a literature review

“…17 Therefore, more and more researchers have begun to pay close attention to it and have demonstrated its ability to inhibit the quorum sensing (QS) system. 17,18 In addition, garlic compounds have also been shown to prevent cardiovascular disease, [19][20][21][22][23] decrease cholesterol and fatty acid levels, [24][25][26] reduce blood pressure, 23,25,27,28 regulate the immune system, 15,28 prevent and treat tumours, 15,[29][30][31] and resist parasites. 32 The similarities and differences between allicin and ajoene are shown in Table 1.…”