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Multi-Step Rearrangement Mechanism for Acetyl Cedrene to the Hydrocarbon Follower†

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Chemistry of Natural Compounds Aims and scope

Conversion of acetyl cedrene (2) to its follower (3) using acetic anhydride and polyphosphoric acid involves a multi-step cationic molecular rearrangement, which is consistent with deuteriation and 1-13C labeling studies of acetyl cedrene. The key step involves cyclopropylcarbinyl cation-cyclopropylcarbinyl cation rearrangement.

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Acknowledgment

We express our deep gratitude to Prof. R. B. Bates and Prof. Mar Gomez Gallego for critical evaluation of the proposed mechanisms and valuable suggestions, and Dr. Nitin Borkar, CEO, VerGo Pharma Research Laboratories Pvt. Ltd., Verna, Goa-403722, India for support.

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Authors and Affiliations

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

    S. K. Paknikar

  2. Department of Science and Environment, Roskilde University, P.O. Box 260, DK-4000, Roskilde, Denmark

    F. S. Kamounah & P. E. Hansen

  3. Department of Chemistry, University of Pune, Pune, 411007, India

    M. S. Wadia

Authors
  1. S. K. Paknikar
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  2. F. S. Kamounah
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  3. P. E. Hansen
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  4. M. S. Wadia
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Corresponding author

Correspondence to S. K. Paknikar.

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†Dedicated to Prof. Sukh Dev on his 91st Birthday.

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2017, pp. 562–565.

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Paknikar, S.K., Kamounah, F.S., Hansen, P.E. et al. Multi-Step Rearrangement Mechanism for Acetyl Cedrene to the Hydrocarbon Follower† . Chem Nat Compd 53, 661–664 (2017). https://doi.org/10.1007/s10600-017-2085-1

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  • DOI: https://doi.org/10.1007/s10600-017-2085-1

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