Studies in marine macrolide synthesis: Synthesis of the C1-C15 subunit of spongistatin 1 (altohyrtin A) and 15,16-anti aldol coupling reactions

Article abstract of DOI:10.1016/S0040-4039(97)10126-5

The C₁-C₁₅ aldehyde 3, containing the AB-spiroacetal of spongistatin 1 (1), was prepared in 17 steps from methyl ketone (S)-8. The C₁₅ and C₁₆ stereocentres could be introduced together, relying on Felkin-Anh control, by using a boron-mediated, anti aldol coupling reaction, as in 22 → 25 and 26.