1981/06/01 by R. B. Woodward, Dale E. Ward, B. W. Au-Yeung +4 · 5 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Carbohydrate Chemistry and Synthesis #Cancer therapeutics and mechanisms #Chemical synthesis and alkaloids
paper · doi:10.1021/ja00401a050
openalex publication_date 1981/06/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02
In reporting a total synthesis of erythromycin (la) we described in the preceding paper1 the synthesis of the erythronolide A seco acid derivative 2 in optically active form. In this paper we wish to report a successful transformation of 2 to 12 (synthetically equivalent to erythronolide A) via lactonization and also demonstrate that the proper functionalization of a substrate is critical for the successful lactonization.