Amino Acids and Serum Proteins by Gould R.F. (ed.)

By Gould R.F. (ed.)

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The synthesis was continued with the mixtury by way of the aldehyde (116) and the thio-acetal (117). Bromination, elimination and introduction of the N(l) malonate residue gave (119) ready for an intramolecular alkylation reaction. ~OAC 0:7 NH YJb --- o;=Q -- M, oP H (ii) (i) H ~ (115) (114) (113) H j (iii) S H~~HR Me . 0 i : :7 S NH ~NHR H (iv) Me ~ H H i 0 :7 CHO NH (116) (117) j (v) H Me ~ H H i 0 :7 NH (118) ""'" H S~NHR (vi) S~HR Me 0:7 (119) 30 R. SOUTHGATE and S. ELSON: j (vii) ~ H Me H H 1 0::7 " S~NHR (viii) M:>:tJJ: 0J-~~ N R R R S~N'" R (120) (121) j (ix) ~ H·.

The Beecham group found that thiols add readily to the double bond of C(2)-unsubstituted l-carbapenems, and this approach has been used to synthesise racemic PS-S (130). The N-silylated 4-allylazetidinone (157) was alkylated with ethyl iodide and the product (158) transformed to the phosphorane (159). Cyclisation to (160) was followed by reaction with acetamidoethane thiol to form three isomers of the addition product (161). These could be converted to ~he carbapenem (162) on reaction with iodobenzene dichloride in the presence of pyridine.

Subsequent esterification followed by elimination of the sulphate residue gave a mixture of isomers of the olefin (100) (70, 75). This rearrangement also occurred with MM 17880 monoester, but not with MM 4550. Elimination of the sulphate moiety of the di-ester (101) of MM 13902 was stereospecific, giving solely the (E)-isomer of the ethylidene derivative (102), suggesting that the configuration in the side-chain was (S). This was subsequently confirmed by X-ray analysis (75). olivaceus, together with the corresponding isomers MM 22381 (105) and MM 22383 (106) having the transarrangement of protons about the ~-lactam ring.

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