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Synlett 1991; 1991(10): 717-718
DOI: 10.1055/s-1991-34775
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Natural 1,2-Dithiolane 1-Oxides. A Synthetic Approach Based on [2+2]-Cycloaddition Reactions with Thiones

Gerald Pattenden* , Anthony J. Shuker
  • *Department of Chemistry, The University, Nottingham NG7 2RD, England
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Publication Date:
13 March 2002 (online)

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[2+2]-Cycloaddition between thioacetone and the ketene intermediate (2-acetoxy-1-propen-1-one) derived from 2-acetoxypropanoyl chloride (6) in the presence of triethylamine, produces the same ß-thiolactone intermediate (5; 3-hydroxy-3,4,4-trimethylthietan-2-one) as that produced by hydrolysis of the adduct 8 from photochemical [2+2]-cycloaddition between thiophosgene and 3-methyl-2-trimethylsiloxy-2-butene (7). The thiolactone 5 is then converted in three steps, via 9 and 10, to the novel 4-hydroxy-4,5,5-trimethyl-1,3-dioxo-1,2-dithiolane residue 4 found in the antibiotic substance leinamycin (3).

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