Enantioselective synthesis of an aziridinomitosane and selective functionalizations of a key intermediate.
An enantioselective synthesis of mitosane core (-)-1 has been achieved. Key steps include a rapid assembly of a key eight-membered-ring intermediate employing ring-closing metathesis. Kinetic resolution of an advanced secondary alcohol was then accomplished by using a peptide-based asymmetric acyl transfer catalyst that was discovered from a parallel screen of catalyst candidates. Optically pure material was then converted to the mitosane core, which was the subject of additional studies on the selective modification to produce several substituted compounds containing a mitosane ring system.
Papaioannou
Nikolaos
N
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.
Blank
Jarred T
JT
Miller
Scott J
SJ
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D007202:Indicators and Reagents; D007510:Isatin / Q000737:chemistry; D016685:Mitomycin / Q000138:chemical synthesis* / Q000737:chemistry; D008937:Mitomycins; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008937:Mitomycins; D010455:Peptides; C435767:mitosane; D016685:Mitomycin; D007510:Isatin