Enantioselective synthesis of a mitosane core assisted by diversity-based catalyst discovery.
[reaction: see text]. Synthesis of mitosane 1 in optically pure form is reported. A retrosynthetic plan that proceeds through racemic allylic alcohol 3 was carried out. This intermediate served as a test substrate for a rapid screen of a small library (152 members) of peptide-based kinetic resolution catalysts. Peptide 9 was found to effect kinetic resolution with k(rel) = 27. Alcohol (-)-3 was then converted to optically pure (-)-1 in eight steps.
Papaioannou
N
N
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.
Evans
C A
CA
Blank
J T
JT
Miller
S J
SJ
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D016685:Mitomycin / Q000138:chemical synthesis* / Q000737:chemistry; D008937:Mitomycins; D008968:Molecular Conformation
D000903:Antibiotics, Antineoplastic; D008937:Mitomycins; C435767:mitosane; D016685:Mitomycin