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 inAngewandte Chemie International Edition Vol. 57; no. 38; pp. 12290 - 12293
Main Authors Silva, Filipa, Khokhar, Shaista S., Williams, Danielle M., Saunders, Robert, Evans, Gareth J. S., Graz, Michael, Wirth, Thomas
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.09.2018
Wiley Subscription Services, Inc
John Wiley and Sons Inc
EditionInternational ed. in English
Subjects
ajoene
allicin
Biological activity
Chemistry
Chemistry, Multidisciplinary
Communication
Communications
Disulfides - chemical synthesis
Disulfides - chemistry
Disulfides - pharmacology
Garlic
Garlic - chemistry
Garlic - metabolism
organosulfur compounds
Physical Sciences
Pseudomonas aeruginosa - drug effects
Pseudomonas aeruginosa - physiology
Quorum Sensing - drug effects
Science & Technology
Selenium - chemistry
selenoxide elimination
Stability
Sulfinic Acids - chemistry
Sulfoxides
Synthesis
garlic
selenoxide elimination
organosulfur compounds
ENHANCEMENT
ajoene
allicin
AGENTS
DISULFIDES
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808605