Two distinct epoxide ring opening pathways in a monocyclic model system of the kedarcidin chromophore

Article abstract of DOI:10.1016/S0040-4039(98)00664-9

Two monocyclic model compounds 2 and 3 were synthesized from (Z)- ketoeneyne 5 for studying the epoxide ring opening pathways related to activation of the kedarcidin chromosphore (1). The solvent-derived SNI products 8a,b and 9a,b were formed from 2 and 3 in MeOH while the S(N)2 products 10a,b were produced from 2 and 3 with methyl thioglycolate in buffer (pH 7.0)-iPrOH; the latter reaction may provide a new scenario for bioreductive activation of the kedarcidin chromophore via an S(N)2 attack of thiol at the propargylic carbon atom.