Synthesis of Alkaloid GB 13
C20H29NO2
Principal investigator | Lewis N. Mander |
---|---|
Publication year | 2003 |
Synthesis type | Total |
Number of steps | 31 (linear) |
References |
Part 1 of 1
+
+
AcOH
H2O
Reflux, 16 h, 89%
MeOCH2Cl,
i-Pr2NEt,
DMAP
CH2Cl2
0 °C to RT, 16 h, 97%
NsN3,
Et3N
MeCN
0 °C to RT, 2 h
Et3N,
Cl3CCOCl
CH2Cl2
0 °C, 5 min, 98%
- i-Pr2NLi , KOt-Bu
- (PhSe)2
THF
0 °C, 100 min
H2O2
EtOAc, H2O, THF
0 °C, 2 h, 74% (2 steps)
n-Bu4N+ F-
THF
0 °C, 60 min, 74%
LiAlH4
Et2O, THF
-78 °C, 5 min, 94%
MeOCH2Cl,
i-Pr2NEt,
DMAP
CH2Cl2
0 °C to RT, 16 h, 96%
HCl
H2O, MeOH, THF
RT, 45 min, 55% (2 steps)
LiAlH4
Et2O
0 °C, 30 min
NH2OH.HCl
Pyr
95 °C, 4 h
NaBH4,
ZrCl4
THF
RT, 16 h
Zn
AcOH, Et2O
RT, 4 h
(CF3CO)2O,
Pyr
CH2Cl2
RT, 3 h, 32% (4 steps)
HCl
Acetone, H2O
50 °C, 16 h
MeOCH2Cl,
i-Pr2NEt,
DMAP
CH2Cl2
0 °C to RT, 16 h, 71%
- i-Pr2NLi
- TMSCl
THF
-78 °C, 35 min
K2CO3
H2O, MeOH
55 °C, 16 h
HCl
Acetone, H2O
55 °C, 20 h, 37% (2 steps)