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. 2018 Sep 17;57(38):12290-12293.
doi: 10.1002/anie.201808605. Epub 2018 Aug 19.

Short Total Synthesis of Ajoene

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Free PMC article

Short Total Synthesis of Ajoene

Filipa Silva et al. Angew Chem Int Ed Engl. .
Free PMC article

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.

Keywords: ajoene; allicin; garlic; organosulfur compounds; selenoxide elimination.

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Block's synthesis of ajoene (2).
Scheme 2
Scheme 2
Synthesis of aryl propyl selenides 6.
Scheme 3
Scheme 3
Radical addition of thioacetic acid to form derivatives 7.
Scheme 4
Scheme 4
Synthesis of ajoene (2).
Figure 1
Figure 1
Inhibition of a Pseudomonas aeruginosa Pa01 lasB‐gfp reporter strain, where a decrease in fluorescence is directly related to QS‐controlled expression.

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