Open AccessAn efficient synthesis of (±)-frondosin B using a Stille–Heck reaction sequence
Author(s) -
KyeSimeon Masters,
Bernard L. Flynn
Publication year - 2010
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/b924542a
Subject(s) - stille reaction , chemistry , trifluoromethanesulfonate , heck reaction , yield (engineering) , sequence (biology) , furan , stereochemistry , organic chemistry , palladium , catalysis , biochemistry , materials science , metallurgy
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.
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