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16a Starting
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16b (-)-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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17b See also: ref. 19
17c
8:
IR (neat): 2981, 2933, 1711, 1639, 1612, 1446, 1367, 1308, 1277,
1213, 1161, 1140, 1039, 991, 879 cm-¹; ¹H
NMR (270 MHz, CDCl3): δ = 7.56
(dd, J = 11.5,
15.2 Hz, 1 H), 5.99 (br dq, J = 1.1, 11.7
Hz, 1 H), 5.76 (d, J = 15.2
Hz, 1 H), 4.20 (q, J = 7.1
Hz, 2 H), 1.89 (d, J = 0.9
Hz, 3 H), 1.88 (s, 3 H), 1.30 (t, J = 7.1 Hz,
3 H); ¹³C NMR (67.8 MHz, CDCl3): δ = 167.7,
146.2, 141.0, 123.7, 118.6, 60.1, 26.5, 18.9, 14.3
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20 Acid-catalyzed epoxide opening of
(±)-7a (cat. H2SO4-MeOH
or BF3˙OEt2-MeOH) resulted
in a ratio of approximately 1:4 to 1:6 (desired/undesired),
which was roughly estimated by ¹H NMR analysis
of the crude products.
21
Nagumo S.
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22b 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.
