Abstract
An efficient synthesis of pyranocoumarins is achieved starting from 2H -pyrans. This process provides naturally occurring seselin, cis -khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer.
Key words
ring-opening - epoxides - nucleophiles - formylations - pyranocoumarin derivatives
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26 Spectral data for 31 : IR (neat): 3053, 2928, 1651, 1593, 1453, 1412, 1348, 1331, 1302, 1263, 1190, 1163, 1136, 1071, 1020, 920: 864 cm
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1 . 1 H NMR (300 MHz, CDCl3 ): δ = 6.44 (1 H, d, J = 10.0 Hz), 5.16 (1 H, d, J = 10.0 Hz), 5.06 (1 H, t, J = 7.1 Hz), 2.40-2.33 (4 H, m), 2.03-1.93 (4 H, m), 1.75-1.68 (2 H, m), 1.65 (3 H, s), 1.54 (3 H, s), 1.34 (3 H, s).