Total Synthesis of Homoseongomycin Enantiomers and Evaluation of Their Optical Rotation.

ABSTRACT: A total synthesis of each homoseongomycin enantiomer was accomplished in 17 total steps (longest linear sequence = 12 steps) and 10 chromatographic purifications. Several schemes were attempted to forge the key 5-membered ring, but only a Suzuki coupling-intramolecular Friedel-Crafts acylation sequence proved viable. Challenges encountered during the optical rotation characterization of the natural product left us with two important takeaways. First, highly colored compounds like homoseongomycin that absorb near/at the sodium d-line may require optical rotation measurements at other wavelengths. Second, high dilution of such compounds to obtain measurement at the sodium d-line could result in artificially large and incorrectly assigned specific rotations. To verify the optica

SUBMITTER: Petruncio G 

PROVIDER: S-EPMC11256097 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature