Approaches to the Synthesis of the Galbulimima Alkaloid Himandrine
Patrick D. O’Connor A , Giuseppe Del Signore A , Matthew M. W. McLachlan A , Anthony C. Willis A and Lewis N. Mander A BA Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
B Corresponding author. Email: mander@rsc.anu.edu.au
Australian Journal of Chemistry 63(10) 1477-1491 https://doi.org/10.1071/CH10252
Submitted: 28 June 2010 Accepted: 6 August 2010 Published: 1 October 2010
Abstract
The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include Diels–Alder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.
Acknowledgements
The authors are grateful to the ANU Graduate School (GSS scholarships awarded to P.D.O. and M.M.W.M.), and the Research School of Chemistry (Alan Sargeson Merit Award to P.D.O. and M.M.W.M.) for generous support.
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