Total synthesis of neurymenolide A based on a gold-catalyzed synthesis of 4-hydroxy-2-pyrones.
Treat me gently: for a selective synthesis of the unusually sensitive cyclophanic α-pyrone neurymenolide A, the chosen catalysts must be able to distinguish between six different sites of unsaturation, without scrambling any of the skipped π systems. This challenge was met with a new gold-catalyzed pyrone synthesis in combination with a molybdenum-catalyzed ring-closing alkyne metathesis.
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany.
Wojciech
W
Chaładaj
Matthieu
M
Corbet
Alois
A
Fürstner
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D018942:Macrolides / Q000378:metabolism*; D008982:Molybdenum / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000378:metabolism*; D013237:Stereoisomerism
D000480:Alkynes; D018942:Macrolides; D011753:Pyrones; C534975:neurymenolide A; D006046:Gold; D008982:Molybdenum