Proposal for structure revision of pinofuranoxin A through total syntheses of stereoisomers.
J Nat Med
; 78(3): 608-617, 2024 Jun.
Article
in En
| MEDLINE
| ID: mdl-38587582
ABSTRACT
The relative configuration of the epoxide functionality in pinofuranoxin A (1), α-alkylidene-ß-hydroxy-γ-methyl-γ-butyrolactone with trans-epoxy side chain isolated by Evidente et al. in 2021, was revised by DFT-based spectral reinvestigations and stereo-controlled synthesis. The present investigation demonstrates the difficulty of the configurational elucidation of the stereogenic centers on the conformationally flexible acyclic side-chains. Sharpless's enantioselective epoxidations and dihydroxylations were quite effective in the reinvestigations of the configurations. As our syntheses made all diastereomers available, these would be quite effective in the next structure-biological activity relationship studies.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
4-Butyrolactone
Language:
En
Journal:
J Nat Med
Year:
2024
Document type:
Article