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Spectral Data
of Selected Compounds
Compound 9:
colorless syrup; [α]D
²5 -37.3
(c 2.0, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 7.35-7.17
(m, 5 H), 7.13 (d, J = 8.4
Hz, 2 H), 6.79 (d, J = 8.4
Hz, 2 H), 4.61 (d, J = 9.7 Hz,
2 H), 4.55-4.39 (m, 2 H), 4.31 (d, J = 7.1
Hz, 2 H), 4.04 (t, J = 7.7
Hz, 1 H), 3.86-3.77 (m, 1 H), 3.77 (s, 3 H), 3.67-3.58
(m, 1 H), 3.58-3.41 (m, 2 H), 3.35 (s, 3 H), 3.29-3.02 (m,
1 H), 2.00-1.75 (m, 2 H), 1.75-1.55 (m, 10 H),
1.40-1.30 (m, 2 H). ¹³C NMR
(75 MHz,CDCl3): δ = 159.0, 137.9, 130.4,
129.2, 128.3, 127.9, 127.7, 113.6, 110.8, 86.3, 82.3, 79.6, 75.3,
72.7, 72.4, 69.5, 66.1, 65.1, 61.0, 57.9, 55.1, 37.0, 35.7, 35.3,
29.6, 24.9. FTIR (neat): 3400, 3090, 2910, 2250, 1110 cm-¹.
ESI-MS: m/z = 539 [M + H]+,
556 [M + NH4]+. Anal.
Calcd for C32H42O7: C, 71.35; H,
7.86. Found: C, 71.41; H, 7.79.
Seco acid 2:
colorless liquid; [α]D
²5 -3.8
(c 3.0, CHCl3).
¹H
NMR (200 MHz, CDCl3): δ = 7.28 (m,
5 H), 4.72-4.49 (m, 4 H), 4.15-4.05 (m, 1 H),
3.82-3.69 (m, 1 H), 3.69-3.60 (m, 1 H), 3.43-3.25
(m, 7 H), 2.66 (dd, J = 15.8,
4.1 Hz, 1 H), 2.51 (dd, J = 15.8,
7.9 Hz, 1 H), 1.87-1.71 (m, 1 H), 1.66-1.38 (m,
5 H), 1.16 (d, J = 6.0
Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 175.7,
138.5, 128.2, 127.9, 127.5, 96.1, 78.2, 74.9, 72.4, 67.7, 58.9,
57.7, 55.5, 34.4, 33.6, 30.0, 24.1, 19.7. FTIR (neat): 3500, 3150,
2930, 1690, 1120 cm-¹. ESI-MS: m/z = 385 [M + H]+,
407 [M + Na]+. Anal.
Calcd for C20H32O7: C, 62.48; H,
8.39. Found: C, 62.61; H, 8.31.
Compound 12b:
colorless syrup; [α]D
²5 -63.3
(c 0.35, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 6.25 (dd, J = 11.3, 5.8
Hz, 1 H), 5.84 (dd, J = 11.3,
1.8 Hz, 1 H), 4.66-4.52 (m, 1 H), 4.13-3.95 (m,
1 H), 3.77 (t, J = 6.9
Hz, 1 H), 3.25 (s,
3 H), 2.34-1.53 (m, 6 H),
1.36 (d, J = 6.2
Hz, 3 H). ESI-MS: m/z = 225 [M + Na]+.
Anal. Calcd for C11H18O4: C, 61.66;
H, 8.47. Found: C, 61.53; H, 8.59.
Compound 13a:
colorless syrup; [α]D
²5 +8.33
(c 0.45, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 7.29 (m,
5 H), 4.81 (d, J = 11.7
Hz, 2 H), 4.67-4.53 (m, 2 H), 4.45 (d, J = 11.7, 1
H), 3.89-3.72 (m, 1 H), 3.46 (m, 1 H), 3.31 (s, 3 H), 3.09 (d, J = 13.5 Hz,
1 H), 2.93 (dd, J = 14.2,
6.6 Hz, 1 H), 2.34-1.69 (m, 2 H), 1.63-1.42 (m,
4 H), 1.18 (d, J = 6.2
Hz, 3 H). ESI-MS: m/z = 345 [M + Na]+.
Anal. Calcd for C18H26O7: C, 67.06;
H, 8.13. Found: C, 67.21; H, 8.02
Compound 14:
colorless syrup; [α]D
²5 +10.7
(c 0.55, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 7.46-7.29
(m, 5 H), 5.18-4.98 (m, 1 H), 4.82 (d, J = 11.3
Hz, 1 H), 4.59 (d, J = 11.3 Hz,
1 H), 4.11 (ddd, J = 11.7,
8.4, 3.6 Hz, 1 H), 3.56 (s, 3 H), 3.46-3.34 (m, 1 H), 2.95-2.59
(m, 3 H), 2.53-2.12 (m, 4 H), 2.05-1.90 (m, 1
H) 1.32 (d, J = 6.6
Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 208.2,
169.2, 132.9. 129.5, 128.3, 127.6, 81.9, 79.6, 72.1, 71.3, 58.9,
43.9, 40.2, 39.6, 33.2, 19.7. FTIR (neat): 3452, 1733, 1726 cm-¹.
HRMS: m/z calcd for C18H24O5NaCl [M + Na]+:
343.1521; found: 343.1512.
Compound 1:
colorless syrup; [α]D
²5 +58.0
(c 0.12, CHCl3). ¹H
NMR (500 MHz, CDCl3): δ = 5.04 (m,
1 H), 4.11 (ddd, J = 11.6,
8.7, 2.9 Hz, 1 H), 3.43 (s, 3 H), 3.35 (ddd, J = 10.2, 8.2,
2.4 Hz, 1 H), 3.09 (br s, 1 H, OH), 2.93 (dd, J = 17.4,
7.7 Hz, 1 H), 2.86 (dd, J = 17.4,
3.4 Hz, 1 H), 2.63 (dd, J = 17.4, 2.9
Hz, 1 H), 2.45 (dd, J = 17.4,
2.4 Hz, 1 H), 2.41 (ddd, J = 13.6,
7.2. 3.8 Hz, 1 H), 2.32 (ddd, J = 14.0,
10.6, 3.4 Hz, 1 H), 2.11 (m, 1 H), 2.02 (m, 1 H), 1.26 (d, J = 6.3 Hz,
3 H). ¹³C NMR (75 MHz, CDCl3): δ = 208.6,
169.2, 81.9, 71.6, 68.3, 57.3, 41.7, 40.4, 39.7, 33.1, 19.6. FTIR
(neat): 3458, 1735, 1726 cm-¹. HRMS: m/z calcd for C11H18O5NaCl [M + Na]+:
253.1051; found: 253.1048.
Compound 15:
colorless syrup; [α]D
²5 -105.3
(c 0.15, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 4.57 (m,
1 H), 4.11-4.06 (m, 1 H), 3.47 (m, 1 H), 3.38 (s, 3 H),
3.18 (d, J = 14.1
Hz, 1 H), 2.79-2.55 (m, 3 H), 2.14 (s, 3 H), 2.04 (dd, J = 9.1, 2.0
Hz, 1 H), 1.96-1.78 (m, 3 H). FTIR (neat): 3442, 1734,
1728 cm-¹. ESI-MS: m/z = 231 [M + H]+.
Anal. Calcd for C11H18O5: C, 57.38;
H, 7.88. Found: C, 57.51; H, 7.76.
13a
Ishigami K.
Wantanabe H.
Kitahara T.
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Fürstner A.
Nagano T.
Müller C.
Seidel G.
Müller O.
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