Santonic acid: Zn–HCl–ether reduction and ceric ammonium nitrate oxidation

Abstract

Reduction of santonic acid using Zn–HCl–ether yielded succinic anhydride derivatives via pinacolisation followed by rearrangement, whereas oxidation of santonic acid using ceric ammonium nitrate afforded five oxidative decarboxylation products.

Dedicated to Prof. TBH McMurry.

Keywords::

• santonic acid
• Zn–HCl–ether reduction
• ceric ammonium nitrate oxidation
• oxidative decarboxylation
• bicyclo[3.3.0]octane

Acknowledgements

We thank Dr Bruno Maurer for recording the NMR spectra of 4 and 5 and his critical comments, Prof. RB Bates for NMR measurements and help in the characterisation of 6–10 and Dr VP Joshi for the MS of 6 and 9. The authors thank the CSIR, New Delhi for the award of a senior research fellowship to KPF. We thank the reviewer(s) for critical evaluation and improving the manuscript.

Notes

^1. Present address: Prof. S.C. Bhattacharyya Organic Synthesis Laboratory, VerGo Pharma Research, Verna, Goa 403722, India.