Stereoselective Methodology for the Synthesis of an Antifungal Allylamine: Terbinafine

Author(s): Bhavna Gupta, B. Ravindra Babu, Kapil Gyanda, Siva S. Panda, Subhash C. Jain.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 2 , 2014

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Abstract:

The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4- yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.

Keywords: Terbinafine, alkylation, stereoselective synthesis, selective reduction, antifungal drug.

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Article Details

VOLUME: 11
ISSUE: 2
Year: 2014
Page: [141 - 144]
Pages: 4
DOI: 10.2174/15701786113106660078
Price: $65

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