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A short approach to cytogenin and first total synthesis of aspergisocoumarin A and fusarimarin C.
- Source :
-
Tetrahedron . Dec2024, Vol. 168, pN.PAG-N.PAG. 1p. - Publication Year :
- 2024
-
Abstract
- A novel, efficient route to the first total synthesis of the bioactive isocoumarins aspergisocoumarin A, fusarimarin C and cytogenin is demonstrated. This approach features a groundbreaking single-step synthesis of isocoumarins utilizing a challenging cross-ester coupling of ethyl dimethoxy orsellinate and ethyl glycolate in the presence of a LiBr-LiTMP complex. The process leverages bromide ion-induced aggregation to facilitate a one-pot tandem reaction sequence: lateral lithiation, acylation, enolization, and lactonization. This innovative method directly produces the isocoumarin moiety with high efficiency. Subsequent transformations include selective BBr 3 -mediated demethylation, oxidation, and Wittig reactions. The streamlined synthetic routes demonstrated: a two-step pathway to cytogenin and a four-step sequence to aspergisocoumarin A and fusarimarin C, achieving overall yields of 37 %, 27 %, and 27 % respectively. [Display omitted] [ABSTRACT FROM AUTHOR]
- Subjects :
- *WITTIG reaction
*ENOLIZATION
*DIHYDROCHALCONES
*OXIDASES
*DEMETHYLATION
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 168
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 180930338
- Full Text :
- https://doi.org/10.1016/j.tet.2024.134343