Recently, we synthesized the proposed structure of the fungal glycolipid fusaroside and suggested corrections in its structure with respect to the positions of the double bonds in the lipid portion. Herein, we report the first total synthesis of the proposed revised structure of fusaroside and thereby confirm its structure. The synthesis involved Julia-Kocienski olefination for the construction of fatty acid and its coupling with trehalose at the O4 position followed by late-stage gem-dimethylation as key steps.
structure, total synthesis, fusaroside, fungal glycolipid, Fusarium sp. LN-11
NCBI PubMed ID: 37291052Publication DOI: 10.1021/acs.joc.3c00167Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: S.S. Kulkarni
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India
Methods: 13C NMR, 1H NMR, IR, TLC, chemical synthesis, UV, optical rotation measurement, CC, HR-ESI-MS, Julia−Kocienski olefination
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