Short Total Synthesis of Ajoene

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 s...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-09, Vol.57 (38), p.12290-12293
Main Authors: Silva, Filipa, Khokhar, Shaista S., Williams, Danielle M., Saunders, Robert, Evans, Gareth J. S., Graz, Michael, Wirth, Thomas
Format: Article
Language:English
Subjects:
ajoene
allicin
Biological activity
Communication
Communications
Disulfides - chemical synthesis
Disulfides - chemistry
Disulfides - pharmacology
Garlic
Garlic - chemistry
Garlic - metabolism
organosulfur compounds
Pseudomonas aeruginosa - drug effects
Pseudomonas aeruginosa - physiology
Quorum Sensing - drug effects
Selenium - chemistry
selenoxide elimination
Stability
Sulfinic Acids - chemistry
Sulfoxides
Synthesis
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Summary: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. Making garlic: An efficient total synthesis of ajoene from easily available starting materials is reported. Upscaling of the procedure enabled the synthesis of ajoene in larger amounts.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808605