Chemistry Reference
In-Depth Information
CH
3
Ac
CH
3
CH
3
H
3
C
H
3
C
H
3
C
O
O
O
O
CH
3
CH
3
CH
3
Ac
2
O
CrO
3
O
O
O
CH
3
H
CH
3
H
CH
3
H
pyr/HCI
H
H
HH
HH
H
Ac
Ac
O
O
O
Diosgenin
AcOH
H
3
C
H
3
C
H
3
C
O
O
O
CH
3
CH
3
CH
3
H
2
/Pd
1) KOH
H
CH
3
CH
3
CH
3
H
H
2) CrO
3
HH
HH
HH
Ac
Ac
O
O
O
Progesterone
FIGURE 10.7
The synthetics steps of the conversion of the steroid aglycone from the yam:
diosgenin into progesterone.
Isolation of Diosgenin Leading to Progesterone
Pretreatment
(Remove soil and microbes; pulverized)
Primary extraction
Water (hydrophilic) + Ether
2nd extraction
n-Butanol (dioscin) + Water
Column chromatography
Purified dioscin
Hydrolysis
Diosgenin
Marker degradation
Progesterone
Column chromatography on silica gel, Eluent—Chloroform:Methanol:Water
(7:1.5:0.1) mixture
Steroids are complex molecules and require careful spectroscopic analysis. For
example, the
13
C NMR of diosgenin, shown in Figure 10.8, reveals all the carbon
resonance signals. The infrared (IR) spectrum is shown in Figure 10.9.
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