Total Synthesis of Antifungal Macrolide Sch 725674

Abstract

Total synthesis of the 14-membered macrolide Sch 725674 has been developed that is based on macrocyclic ring closure either by Yamaguchi or Shiina macrolactonization and the con-struction of the precursor seco acid by Pd(OH) 2 transformation of primary propargyl alcohol/HWE olefination between two fragments is shown.

Stereoselective synthesis of marine macrolide Aspergillide D

“…Oxidation of the primary alcohol with Dess-martin periodinane in CH2Cl2 gave the corresponding aldehyde and was immediately reacted with the C2-ylide in a Wittig reaction resulting in the α,β-unsaturated ester 30 in good yield. Finally, the TBDPS group in compound 15 was deprotected using HF•Pyridine 31,32 in THF at room temperature to afford the secondary alcohol 16 in very good yield.…”

Determination of the Absolute Configuration of Gliomasolide D through Total Syntheses of the C-17 Epimers

“…However, gliomasolide A ( 1 ) showed moderate cytotoxic activity against HeLa (human epithelial carcinoma cell line) cells . Because of the interesting structure and biological activity, the natural product Sch-725674 has been a popular target for synthesis and has attracted the attention of many researchers including our group . Considering structural similarities between compound 6 and the new gliomasolide family, we became interested in this class of compounds.…”