Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17- C32 subunit of scytophycin C

Article abstract of DOI:10.1016/S0040-4039(00)73994-3

The C_17-C₃₂ subunit 8 of scytophycin C was prepared in 11 steps (19% yield, 83% ds) from (S)-12. Key features include the dipropionate aldol construction of the stereopentad 11, the Brown asymmetric crotylboration leading to 10, followed by their Ba(OH)²-induced, Horner-Emmons coupling to give 23, and the BF₃·OEt₂-promoted allylation, 25 → 26.