Synthesis of Alkaloid GB 13

C20H29NO2
Principal investigator | Lewis N. Mander |
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Publication year | 2003 |
Synthesis type | Total |
Number of steps | 31 (linear) |
References |
Part 1 of 1
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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)
