A total synthesis of the unqiue spiroketal natural product talaromycin B (1) is reported. This molecule, produced in nature by the toxicogenic fungus Talaromyces stipitatus, was constructed in the laboratory from the isoxazoline 6 generated (Figure presented.) on reacting the oxime 4 with the olefin 5 in the presence of NaOCl/Et3N/H2O/CH2Cl2. The synthesis scheme is sufficiently flexible and efficient so as to be of practical use in the preparation of suitable quantities of this material for biological evaluation.
ASJC Scopus subject areas
- Colloid and Surface Chemistry