Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine | Zendy

Michael Dlugosch | Zendy; Martin G. Banwell | Zendy

Open Access

Synthesis of a Highly Functionalised and Homochiral 2-Iodocyclohexenone Related to the C-Ring of the Polycyclic, Indole Alkaloids Aspidophytine and Haplophytine

Author(s) -

Michael Dlugosch,

Martin G. Banwell

Publication year - 2018

Publication title -

australian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.319

H-Index - 77

eISSN - 1445-0038

pISSN - 0004-9425

DOI - 10.1071/ch18267

Subject(s) - chemistry , biocatalysis , ring (chemistry) , indole test , stereochemistry , enantiomer , indole alkaloid , diol , alkaloid , green chemistry , cyclohexenone , metabolite , palladium , enantioselective synthesis , organic chemistry , supramolecular chemistry , reaction mechanism , crystal structure , catalysis , biochemistry

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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