PURPOSE: To obtain a synthetic intermediate for antibiotic C-2 substd. carbapenems, by reacting a carbapenem compound with an organostannane in an aprotic polar coordination solvent in the presence of a palladium compound and a halogen compound.
CONSTITUTION: A carbapenem compound of formula I [R is H or CH3; R1 and R2 are each H, CH3, C2H5, R4OCH2, CH3CH(OR4), or CH3CF2 (R4 is H or R5; R5 is triorganosilyl, allyloxycarbonyl, etc.), etc.; Y is allyl, benzyl, alkyl or triorganosilyl; X is trifluoromethanesulfonyloxy, methanesulfonyloxy, Cl, Br, etc.], is treated with an organostannane of formula II (Rs is lower alkyl; R3 is alkyl, alkenyl, phenyl, furyl, etc.), in an aprotic polar coordination solvent in the presence of a palladium compound, a halogen compound and optionaly, a phosphine of formula III (Rp is phenyl, 2-furyl or 2-thienyl), thereby to obtain compound of formula IV.
MAAKU ERU GURIINRII
FURANKU PII DEINITSUNO
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