A Stereospecific Approach to cis-anti-cis Triquinanes

Abstract

A methodology for the synthesis of compounds containing the cis-anti-cis fused triquinane system has been developed starting from tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-(exo)ol 6 involving Ireland ester Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions as key steps.

Keywords:

• Triquinanes
• Ireland-Claisen rearrangement
• Intra-molecular cyclopropanation
• Regiospecific cyclopropane reductive cleavage

Acknowledgments

We thank the Head, R.S.I.C., I.I.T., Madras for NMR and mass spectra of some of the compounds. N.P. is grateful to Prof. T. R. Govindachari and Dr. S. Narasimhan, Centre for Agrochemical Research, SPIC Science Foundation, Madras for their encouragement. T.J.R is grateful to the University Grants Commission, New Delhi for the award of a research fellowship.