# Synthesis of ω-Methylsulfinyl- and ω-Methylsulfonylalkyl Glucosinolates

## TL;DR

This paper describes new methods to synthesize specific types of plant compounds called glucosinolates, which are important for their potential health benefits.

## Contribution

The paper introduces two general synthetic pathways for ω-methylsulfinyl- and ω-methylsulfonylalkyl glucosinolates.

## Key findings

- Selective S-oxidation of ω-methylsulfanyl analogs produced sulfoxide or sulfone counterparts in moderate yields.
- A nitronate chlorination strategy enabled the preparation of key intermediates for coupling with glucopyranose.
- The methods yielded target compounds like glucoraphanin for future bioactivity studies.

## Abstract

General pathways were devised to synthesize ω-methylsulfinyl- and ω-methylsulfonylalkyl glucosinolates, which represent an important class of structurally homogeneous plant specialized metabolites. The first approach was based on the selective S-oxidation of ω-methylsulfanyl analogs previously obtained in our laboratory, producing the corresponding sulfoxide or sulfone counterparts in moderate yields. In an alternative approach, previously prepared ω-nitroalkyl methylsulfide precursors were selectively oxidized either to sulfoxides or to sulfones. The key-thiofunctionalized hydroximoyl chloride intermediates were prepared in situ from sulfoxides or sulfones using a nitronate chlorination strategy. A coupling reaction with 1-thio-β-d-glucopyranose was directly applied, followed by O-sulfation of the intermediate thiohydroximates. The final deprotection of the sugar moiety produced the target compounds, including renowned glucoraphanin and homologs, intended for further bioactivity investigations.