Tetrahedron letters

A novel and efficient synthesis of the key intermediate of 1β-methylcarbapenem antibiotics from (s)-methyl 3-hydroxy-2-methylpropionate

T Kawabata, Y Kimura, Y Ito, S Terashima, A Sasaki…

Index: Kawabata; Kimura; Ito; et al. Tetrahedron Letters, 1986 ,  vol. 27,  # 51  p. 6241 - 6244

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Citation Number: 35

Abstract

A highly efficient synthesis of the key intermediate 2 of 1β-methylcarbapenems was accomplished in 10 steps and 30% overall yield starting from commercially available ( )-methyl 3-hydroxy-2-methylpropionate. The explored synthetic scheme features the addition reaction of diketene with a chiral imine as a key diastereoselective step. ... )-ethyl lactate was found to proceed with a high stereoselectivity similar to that observed for 4i. The formed optically ...