Ring enlargement by alkylated 3-hydroxybutyrates: A synthesis of (12S, 13R)-(-)-12-methyl-13-tetradecanolide

Article abstract of DOI:10.1016/0040-4020(95)00664-T

TBS-protected iodo alcohols 6 were prepared via Frater alkylation and applied in the synthesis of optically active macrolides 5 and 10. By ring enlargement of cyclodecanone (7) the superposition molecule 5 of two macrocyclic odorants was synthesized and a conformationally fixed tricyclic macrolide 11 constructed.