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Synthesis 1996; 1996(8): 981-985
DOI: 10.1055/s-1996-4318
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Direct Synthesis of Keto Nitroaliphatics via Retro-Henry Reaction of Cyclic 2-Nitroalcohols by Anhydrous Copper Sulfate Adsorbed on Silica Gel. A Short Synthesis of (±)-Phoracantholide I

Anil K. Saikia, Monoj J. Hazarika, Nabin C. Barua* , Maitreyee Sarma Bezbarua, Ram P. Sharma, Anil C. Ghosh
  • *Organic Chemistry Division, Regional Research Laboratory, Jorhat-785 006, Assam, India, Fax +91(0376)321158
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Publication Date:
31 December 2000 (online)

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It has been observed that anhydrous CuSO4 adsorbed on silica gel effects the C-C bond cleavage between the hydroxy group and the nitro group of 2-nitroalcohols. In the case of 2-nitrocyclohexanols, the products are RCO(CH2)4CH2NO2 where R is alkyl, aryl, etc. This strategy has been applied for a short synthesis of (±)-phoracantholide I.

C-C bond cleavage - 2-nitroalcohols - copper sulfate-silica - Phoracantholide