Download PDF
Synlett 1991; 1991(10): 717-718
DOI: 10.1055/s-1991-34775
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
13 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

[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).