AbstractMichael additions and reactions with haloalkanes have demonstrated the synthetic usefulness of the C-2 and C-4 anions in ceph-3-em sulphides and sulphoxides for the formation of a range of novel compounds (A-H). Other compounds prepared from similiar reactions include (I-O).
A reverse Michael addition was attempted on the C-4 mono-adducts (M) and (N) and di-adducts (L) and (O).
Determination of the configuration of the di-adducts (F) and (I) was accomplished by de-esterification followed by decarboxylation and resulted in the novel ceph-3-em (P).
Conversion of (J) and (K) into novel ceph-3-ems (Q) and (R) bearing C-2 exocyclic bond systems via a Pummerer rearrangement is described. Attempts at a Pummerer rearrangement of (D) and (E) failed.
Numerous attempts at a Cope rearrangement on ceph-2-em sulphoxide (G) and sulphide (H) failed.
De-esterification reactions of the new ceph-3-ems to their corresponding acids were unsuccessful.
|Date of Award||Jun 1995|
|Supervisor||David H. Bremner (Supervisor)|