A short and efficient synthesis of honokiol via Claisen rearrangement |
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Authors: | B.V. Subba Reddy R. Nageshwar Rao N. Siva Senkar Reddy R. Somaiah J.S. Yadav Ravi Subramanyam |
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Affiliation: | 1. Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Colgate Palmolive Technology Center, 909 River Road, Piscataway, NJ, USA |
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Abstract: | A concise and efficient total synthesis of honokiol, a biphenyl-type neolignan is accomplished in six steps using readily available and cost-effective reagents. The synthetic route involves mainly the Grignard reaction, iodine mediated aromatization, and Claisen rearrangement as key steps. A predominant formation of honokiol (1a) was observed in the Claisen rearrangement under microwave irradiation whereas the isohonokiol (1b) was formed as a major product under conventional conditions. |
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Keywords: | Honokiol Grignard reaction Aromatization Claisen rearrangement Microwave irradiation |
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