Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques.
The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.
Jones
Matthew T
MT
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Schwartz
Brett D
BD
Willis
Anthony C
AC
Banwell
Martin G
MG
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D001969:Bromobenzenes / Q000737:chemistry; D018360:Crystallography, X-Ray; D004798:Enzymes / Q000737:chemistry; D009579:Nitrobenzoates / Q000737:chemistry; D010617:Phenanthridines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
D047151:Amaryllidaceae Alkaloids; D001969:Bromobenzenes; D004798:Enzymes; D009579:Nitrobenzoates; D010617:Phenanthridines; C032036:bromobenzene; C015330:lycorine