Stereoselective Methodology for the Synthesis of an Antifungal Allylamine: Terbinafine

Title:Stereoselective Methodology for the Synthesis of an Antifungal Allylamine: Terbinafine

Volume: 11 Issue: 2

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

Affiliation:

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

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.

Cite this article as:

Gupta Bhavna, Babu Ravindra B., Gyanda Kapil, Panda S. Siva and Jain C. Subhash, Stereoselective Methodology for the Synthesis of an Antifungal Allylamine: Terbinafine, Letters in Organic Chemistry 2014; 11 (2) . https://dx.doi.org/10.2174/15701786113106660078