2-Amino-2-phenylethan-1-ol → (R)-(-)-5-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone

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Reaction Steps

(R)-(−)-5-[(1,1′-Biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone was prepared in an analogous manner as described for (S)-(+)-5-[(1,1′-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone starting with 1.9 g (5.0 mmol) of the diastereomerically pure salt of (R)-(−)-2-[(1,1′-biphenyl)-4-yl]-2-hydroxypropionic acid and (S)-(+)-phenylglycinol to provide 280 mg (19% yield) of(R)-(−)-5-[(1,1′-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone as a white crystalline material: mp 197-199° C. dec. (CHCl3/hexanes); [α]25D−182° (c=1.42; MeOH); 1H NMR (acetone-d6) δ 7.65-7.41 (m, 9H), 1.89 (s, 3H). Anal Calcd for C17H14O4+0.25 H2O: C, 71.20; H, 5.10. Found: C, 71.19; H, 4.74.

Provenance & Evidence