Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin.
Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine alkene.
Jones
Matthew C
MC
School of Chemistry, University of Leeds, Leeds LS2 9JT, United Kingdom.
Marsden
Stephen P
SP
D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D013379:Substrate Specificity
C532599:2-epi-myriocin; D005229:Fatty Acids, Monounsaturated; D007166:Immunosuppressive Agents