Efficient Approach to 4‐Benzyl‐5,5‐dimethyldihydrofuranones: Total Synthesis of (±_bold;)‐Solafuranone

Abstract

A six‐step general and very efficient synthesis of 4‐(arylmethyl)‐5,5‐dialkyldihydrofuranones starting from corresponding aryl aldehyde has been developed. Solafuranone, a novel furanone isolated from the Chinese folk medicine Solanum indicum, has been accomplished starting from 2,6‐dimethylbenzaldehyde in six steps in an overall yield of 70%. Contrary to expectations, solafuranone and its analogue failed to exhibit any significant cytotoxicity against A549 (lung adenocarcinoma) and HL60 (leukemia cells) cell lines.

Keywords:

• cytotoxicity
• dihydrofuranone
• lycifuranones A and B
• solafuranone
• Solanum indicum

Acknowledgments

We thank the Department of Biotechnology, New Delhi for the financial support, Council of Scientific and Industrial Research, New Delhi, for the award of a research fellowship to G.S. and Indian Academy of Sciences, Bangalore, for providing a summer fellowship to U.D. We are also grateful to Dr. Kondaiah and C. K. Aravinda, Department of Molecular Reproduction, Development and Genetics, Indian Institute of Science, for carrying out the biological evaluation of solafuranone and its analogues.