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DOI: 10.1055/s-0029-1219807
Catalytic Activity Studies of Aminocarbonyl Group Containing Hoveyda-Grubbs-Type Complexes for the Syntheses of Herbarumin I and Stagonolide A
Publication History
Publication Date:
09 April 2010 (online)
Abstract
The catalytic activity of four aminocarbonyl group containing ‘boomerang’-type ring-closing metathesis catalysts have been studied for ten-membered lactone and compared well with the Grubbs I and II as well as the Hoveyda-Grubbs catalysts. The activity was found to be superior to the above three ring-closing metathesis catalysts and suggesting novel stereoselective total syntheses of herbarumin I and stagonolide A.
Key words
decanolides - stagonolides - herbarumin I - Wittig reaction - ring-closing metathesis
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References and Notes
Analytical and
Spectral Data of 10
[α]D
²5 +7.6
(c 1.1, CHCl3). IR (neat):
3455, 2924, 2852, 2097, 1461 cm-¹. ¹H
NMR (300 MHz, CDCl3): δ = 7.43-7.19
(m, 5 H), 6.05 (m, 1 H), 5.34 (dd, J = 17.3,
1.5 Hz, 1 H), 5.18 (dd, J = 10.6,
1.5 Hz, 1 H), 4.60 (ABq, J = 13.6,
11.3 Hz, 2 H), 4.31 (t, J = 5.3
Hz, 1 H), 3.74 (m, 1 H), 3.25 (t, J = 6.04
Hz, 1 H), 2.90 (br s, 1 H), 2.59 (br s, 1 H), 1.69-1.24 (m,
4 H), 0.92 (t, J = 6.8
Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 137.7,
137.9, 137.7, 128.4, 127.8, 128.1, 116.1, 84.2, 73.9, 73.7, 72.6,
35.3, 18.8, 14.0. HRMS: m/z calcd
for C15H22O3Na: 273.1466; found:
273.1472.
Analytical and
Spectral Data of 11
[α]D
²5 +27.0
(c 0.7, CHCl3). IR (neat): νmax = 3398,
2963, 2925, 2855, 1723, 1711, 1639, 1461, 1129 cm-¹. ¹H
NMR (300 MHz, CDCl3): δ = 7.38-7.23
(m, 5 H), 6.02-5.68 (m,
2 H), 5.29-5.12
(m, 2 H), 5.07-4.95 (m, 2 H), 4.66 (ABq, J = 17.2,
11.5 Hz, 2 H), 4.21-4.06 (m, 2 H), 3.50 (t, J = 4.7 Hz,
1 H), 2.33-2.24 (m, 2 H), 2.14-2.06 (dd, J = 7.4, 6.9
Hz, 2 H), 1.78-1.63 (m, 4 H), 1.40-1.22 (m, 2
H), 0.96-0.84 (m, 12 H), 0.07 (s, 3 H), 0.04 (s, 3 H). ¹³C
NMR (75 MHz, CDCl3): δ = 172.7, 138.5,
138.1, 137.6, 128.2, 127.8, 127.5, 116.5, 115.3, 83.9, 74.6, 74.0,
73.7, 34.9, 33.7, 33.1, 31.5, 25.8, 24.1, 18.7, 14.0, -4.2, -5.0.
HRMS: m/z calcd for C27H44O4NaSi:
483.2906; found: 483.2914.
Analytical and
Spectral Data of 12
[α]D
²5 +18.2
(c 1.0, CHCl3). IR (film): νmax = 4272,
3801, 3471, 2954, 1722, 1641, 1371, 1217, 1091 cm-¹. ¹H
NMR (300 MHz, CDCl3): δ = 7.40-7.30
(m, 5 H), 5.68-5.57 (m, 1 H), 5.50 (dd, J = 15.7,
1.1 Hz, 1 H), 5.21 (dt, J = 9.5,
1.1 Hz, 1 H), 4.73-4.53 (m, 3 H), 3.37 (dd, J = 9.6, 1.9
Hz, 1 H), 2.34-2.27 (m, 2 H), 2.03-1.78 (m, 4
H), 1.49 (m, 1 H), 1.36-1.22 (m, 4 H), 0.89 (t, J = 7.4 Hz,
3 H). ¹³C NMR (75 MHz, CDCl3): δ = 175.5,
137.3, 133.1, 130.3, 128.5, 128.0, 124.6, 80.9, 72.3, 68.8, 68.8,
34.5, 33.6, 33.5, 24.5, 17.8, 13.9. HRMS: m/z calcd
for C19H26O4Na: 341.1728; found: 341.1722.
General Procedure
for the Metathesis Reaction
To a stirred solution
of diene (1.0 mmol) in freshly prepared dry CH2Cl2 (200
mL) at r.t. was added the metathesis catalyst (0.01 mmol) under
argon. The progress of the reaction was monitored by TLC. After
completion of the reaction, solvent was removed under reduced pressure.
The crude product was purified by flash column chromatography (EtOAc-hexane = 1:6)
to afford the E-isomer as the sole product.
Analytical and
Spectral Data of 2
[α]D
²5 +10.6
(c 1.0, EtOH); lit.:7b [α]D
²0 +10.8
(c 0.51, EtOH). ¹H
NMR (300 MHz, CDCl3): δ = 5.61 (d, J = 15.9 Hz,
1 H), 5.49 (m, 1 H), 4.95 (td, J = 9.4,
2.2 Hz, 1 H), 4.42 (br s, 1 H), 3.51 (d, J = 9.8
Hz, 1 H), 2.76 (br s, 1 H), 2.45-2.25 (m, 2 H), 2.06-1.81
(m, 4 H), 1.56 (m, 1 H), 1.43-1.18 (m, 3 H), 0.91 (t, J = 7.3 Hz,
3 H). ¹³C NMR (75 MHz, CDCl3): δ = 176.3,
130.7, 124.6, 73.6, 73.3, 70.1, 34.4, 33.6, 33.3, 24.6, 17.9, 13.8.
IR (neat): νmax = 3455, 3038, 2955, 2920,
2867, 1711, 1639, 1219 cm-¹. HRMS: m/z calcd for C12H20O4Na:
251.1259; found: 251.1264.
Analytical and
Spectral Data of 1
Mp 71-72 ˚C; [α]D
²5 -59.2
(c 0.5, EtOH). ¹H
NMR (300 MHz, CDCl3): δ = 6.42 (d, J = 16.0 Hz,
1 H), 6.32 (m, 1 H), 4.65 (dt, J = 9.5,
2.4 Hz, 1 H), 4.05 (dd, J = 9.5,
6.2 Hz, 1 H), 3.57 (d, J = 6.2
Hz, 1 H), 2.57-2.41 (m, 2 H), 2.20-1.90 (m, 6
H), 1.43-1.18 (m, 3 H), 0.93 (t, J = 7.2
Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 199.5,
174.2, 143.1, 131.9, 76.5, 74.4, 34.2, 34.0, 33.5, 24.9, 18.0, 13.7.
IR (neat): νmax = 3468, 2925, 1740,
1700, 1638, 1219 cm-¹. HRMS: m/z calcd for C12H19O4:
227.1278; found: 227.1274.