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Synlett 2011(6): 805-808
DOI: 10.1055/s-0030-1259718
DOI: 10.1055/s-0030-1259718
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of ‘Spacer’-Naproxen [2-(6-Methoxybiphenylen-2-yl)propanoic Acid] and -Isonaproxen [2-(7-Methoxybiphenylen-2-yl)propanoic Acid]
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Publikationsverlauf
Received
28 January 2011
Publikationsdatum:
08. März 2011 (online)


Abstract
The CpCo(CO)2-catalyzed cocyclization of 1,2-diethynyl-4-methoxybenzene with alkynes can be applied to the synthesis of ‘spacer’-naproxen [2-(6-methoxybiphenylen-2-yl)propanoic acid] and its 7-methoxy isomer, ‘spacer’-isonaproxen. While unsymmetrical alkynes are incorporated without regioselectivity, the methoxy group in 6-methoxy-2,3-bis(trimethylsilyl)biphenylene directs electrophiles to C-3, thus allowing for regiochemical differentiation between the 2- and 3-positions.
Key words
alkynes - cobalt - cyclization - carbocycles - regioselectivity
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