Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine
Michael Dlugosch A and Martin G. Banwell A B
+ Author Affiliations
- Author Affiliations
A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
B Corresponding author. Email: Martin.Banwell@anu.edu.au
Australian Journal of Chemistry 71(8) 573-579 https://doi.org/10.1071/CH18267
Submitted: 2 June 2018 Accepted: 13 July 2018 Published: 17 August 2018
Abstract
The enzymatically-derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 10 steps into cyclohexenone 8. The latter compound embodies the enantiomeric form of the C-ring associated with the hexacyclic framework of the alkaloid aspidophytine (2). As such, this work sets the stage for effecting the conversion of the enantiomeric metabolite ent-7 into compound ent-8, and thence, through previously established protocols, including a palladium-catalysed Ullmann cross-coupling reaction, into the title alkaloids.
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