An efficient synthesis of (+/-)-frondosin B using a Stille-Heck reaction sequence.
A concise, convergent synthesis of (+/-)-frondosin B has been developed based on the application of a Stille-Heck reaction sequence of 2-chloro-5-methoxybenzo[b]furan-3-yl triflate and 2-(3-butenyl)-3-(trimethylstannyl)cyclohex-2-enone giving the racemic natural product in a 34% overall yield.
Masters
Kye-Simeon
KS
Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, 381 Royal Parade, Parkville, VIC 3052, Australia.
Flynn
Bernard L
BL
D003512:Cyclohexanones / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D016209:Interleukin-8 / Q000037:antagonists & inhibitors; D008698:Mesylates / Q000737:chemistry; D013237:Stereoisomerism
D003512:Cyclohexanones; D006576:Heterocyclic Compounds, 4 or More Rings; D016209:Interleukin-8; D008698:Mesylates; C421322:frondosin B