309249-44-3Relevant academic research and scientific papers
Synthesis of penicillin N and isopenicillin N
Lau, Rute Madeira,Van Eupen, Jacques T.H.,Schipper, Dick,Tesser, Godefridus I.,Verweij, Jan,De Vroom, Erik
, p. 7601 - 7606 (2000)
Enantiomeric 2-(N-allyloxycarbonyl)aminoadipic acid 1-allyl esters were obtained from the corresponding 2-(N-trityl)aminoadipic acid diallyl esters following selective hydrolysis of the allyl 6-ester group and subsequent exchange of the trityl group by the allyloxycarbonyl function. The resulting monoacids were used to acylate 6-aminopenicillanic acid allyl ester using a carbodiimide-mediated coupling. The products, the L- and D-isomers of 6-[6-(2-(N-allyloxycarbonyl) aminoadipyl)]aminopenicillanic acid diallyl ester were deprotected in one step by catalytic allyl transfer using tetrakis-(triphenylphosphine)palladium(0), to afford isopenicillin N and penicillin N, respectively. The presented straightforward route to penicillin N and isopenicillin N is uniquely compatible with the sensitive nature of the condensation products and gives entry to a new and high yielding procedure that is superior to existing approaches. (C) 2000 Elsevier Science Ltd.
