Novel Concise Synthesis of (±)-Noviose and l-(+)-Noviose by Palladium-Catalyzed Epoxide Opening

Abstract

We established a novel, concise synthetic route for obtaining noviose, the deoxy sugar component of aminocoumarin antibiotics. l-(+)-Noviose was successfully synthesized by utilizing a palladium-catalyzed epoxide-opening reaction and the subsequent lactone formation as key reactions, starting from a nonsugar chiral epoxide, which is easily available in both enantiomeric forms.

noviose - novobiocin - aminocoumarin antibiotics - palladium-catalyzed epoxide opening

References

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(-)-7b: [α]_D ^²6.9 -33.2 (c 1.05, CHCl₃) {Lit.^¹6 [α]_D ^²0 -30.64 (c 1.155, CHCl₃)}; IR (neat): 2954, 1724, 1657, 1437, 1379, 1319, 1296, 1263, 1173, 980, 804 cm^-¹; ^¹H NMR (270 MHz, CDCl₃): δ = 6.84 (dd, J = 6.5, 15.7 Hz, 1 H), 6.12 (dd, J = 1.1, 15.6 Hz, 1 H), 3.76 (s, 3 H), 3.33 (dd, J = 0.9, 6.4 Hz, 1 H), 1.41 (s, 3 H), 1.29 (s, 3 H); ^¹³C NMR (67.8 MHz, CDCl₃): δ = 166.1, 143.1, 124.4, 62.1, 61.7, 51.7, 24.6, 18.6

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This article was occasionally quoted as the reference for the synthesis of (±)-noviose by mistake, which, however, certainly includes ^¹H NMR data of synthesized methyl dl-novioside along with those of naturally derived noviose.