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The stereochemistry of alcohols 5 and 6 was established by an IR study in dilute (0.1 M) CCl4 solution and a 1D NOESY experiment. Trans hydroxy ester 6 showed two equally intense peaks at 1734 cm-1 (free carbonyl) and 1711 cm-1 (hydrogen bonded carbonyl, whereas cis hydroxy ester 5 showed one medium peak at 1734 cm-1 (free carbonyl) and a very strong peak at 1716 cm-1 (hydrogen bonded carbonyl).9 In a 1D NOESY experiment, irradiation of the CHOH hydrogen at δ 4.14 in 6 showed NOEs to the hydroxy hydrogen at δ 2.77 and the ring hydrogens at δ 1.88-1.76. Irradiation of the CHOH hydrogen at δ 3.79 in 5 showed NOEs to the hydroxy hydrogen at δ 3.28 and the allylic side chain methylene group at δ 2.52-2.40 establishing that the hydrogen is cis to the prenyl side chain
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