ASYMMETRIC SYNTHESES OF MOIRAMIDE-B AND ANDRIMID

The first highly diastereoselective asymmetric syntheses of moiramide B 2 and andrimid 3 have been achieved using lithium amide (R)-6 and py rrolidinone auxiliary (R)-9. Pyrrolidinone auxiliary (R)-9 was used to create the novel (S)-3-methyl-N-benzyloxysuccinimide (S)-11 which was subsequently acylated with the highly reactive tert-butoxycarbonyl-pr otected N-carboxy anhydride of L-valine (Boc-val-NCA) (S)-19 under str ongly basic conditions, without racemisation. Lithium amide (R)-6 was used to synthesise homochiral D-beta-phenylalanine tert-butyl ester 25 .