An approach to the C-13 to C-21 sector of the immunosuppressive marine
natural product discodermolide (1) is described. The C-15 to C-16 bon
d is formed by diastereoselective alkylation of a ketone enolate. Eith
er diastereomer of allkylation Can be obtained by selecting the approp
riate counter ion. The C-16 to C-21 subunit is prepared in two steps f
rom 11.