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. 2017 Nov 28;22(12):2081. doi: 10.3390/molecules22122081

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© 2017 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 2 — Synthesis of difluoroallicin (12) from 1-chloro-2-fluoro-2-propene (9) by way of thioacetate 10 and bis(2-fluoro-2-propenyl) disulfide (11), synthesis of S-2-fluoro-2-propenyl-l-cysteine (13) from 9, conversion of 12 to vinyl dithiins 16 and 17 via 2-fluorothioacrolein (15) with loss of 2-fluoro-2-propenesulfenic acid (14), conversion of 12 to trifluoroajoene 18, Diels-Alder trapping of 15 with ethyl acrylate giving thiopyrans 19 and 20, conversion of 11 to polysulfane mixture 21 and conversion of 13 to (+)-S-2-fluoro-2-propenyl-l-cysteine S-oxide (22).