MgSO to produce 8 (0.59 g, 53%), R 0.25 (system 7), mp 110.20°C. UV spectrum: 242.84 nm (log ꢅ 3.2). IR spectrum
4
f
–
1
(
ꢆmax, cm ): 3433.67 (OH), 1650.97 (7-en-6-ketone), 1716.71 (ester), 1226.37, 1149.45 (C–O–C). Table 1 lists characteristic
resonances in the PMR and C NMR spectra of 8.
1
3
2
0-Hydroxy-22-O-succinylecdysone (10). A solution of succinic anhydride (3.6 g, 36 mmol) in Py (8 mL) was
stirred on a magnetic stirrer, cooled with cold water, treated with 2 (2.0 g, 3.85 mmol) and worked up by a method analogous
to that used above for 6. The dry residue was purified over silica gel with elution by hexane–EtOAc to afford 9 (2.7 g, 32.7%),
Rf 0.25 (system 7), mp 177.4°C.
The isopropylidene protection was removed from 9 (1.0 g) in AcOH (70%, 10 mL) at 45°C over 2 h to produce 10
–
1
(
0.56 g, 50.1%), R 0.11 (system 7), mp 146.9°C. UV spectrum: 242.41 nm (log ꢅ 3.9). IR spectrum (ꢆ, cm ): 3379.33 (OH),
f
1
638.18 (7-en-6-ketone), 1714.56 (ester), 1232.06, 1115.01 (C–O–C). Table 1 lists characteristic resonances in the PMR and
1
3
C NMR spectra of 10.
5-O-Butyryl-20-hydroxyecdysone (12). A solution of butyric anhydride (0.064 g, 4.0 mmol) in Py (8 mL) was
stirred on a magnetic stirrer, cooled with cold water, treated with 20-hydroxy-2,3,20,22-di-O-isopropylideneecdysone (4,
2
0
.056 g, 1.00 mmol), stirred at room temperature until the starting compound disappeared, treated with H O (1 mL), stirred for
2
1
h, treated with H O, and evaporated in a rotary evaporator to remove the Py and afford 11 (0.037 g, 58.67%), R 0.38 (system 7),
2
f
mp 204.1°C.
Compound 11 (0.037 g) was treated with H O (30 mL), acidified to pH 4 with HCl solution (10%), left at room
2
temperature until starting 11 disappeared, poured into H O, and extracted with EtOAc (2 ꢂ 25 mL) to afford 12 (0.028 g,
2
–
1
4
4.4%), R 0.25 (system 7), mp 150.8°C. UV spectrum: 245.03 nm (log ꢅ 3.8). IR spectrum (ꢆmax, cm ): 3363.84 (OH),
f
1
653.06 (7-en-6-ketone), 1686.31 (ester), 1211.12, 1110.12 (C–O–C). Table 1 lists characteristic resonances in the PMR and
C NMR spectra.
1
3
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092