Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 37291052Publication DOI: 10.1021/acs.joc.3c00167Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: S.S. Kulkarni <suvarn
chem.iitb.ac.in>
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India
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
Structure type: monomer ; 693.3451 [M+Na]+
C
34H
54O
13Location inside paper: Fig. 1, scheme 4, p. S10, fusaroside (1a)
Trivial name: fusaroside
Compound class: glycolipid
Methods: 13C NMR, 1H NMR, IR, TLC, chemical synthesis, UV, optical rotation measurement, column chromatography, HR-ESI-MS, Julia−Kocienski olefination
Synthetic data: chemical
Comments, role: the revised structure of fusaroside; The spectroscopic data of the synthetic fusaroside 1a (1H, 13C, COSY, HSQC) perfectly matched with the spectral data of the isolated compound.
NCBI Taxonomy refs (TaxIDs): 5506
Show glycosyltransferases
1H NMR data: present in publication
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13C NMR data: present in publication
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There is only one chemically distinct structure:
Found 
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