Synthesis of Gymnomitrol

C15H24O
Principal investigator | Robert M. Coates |
---|---|
Publication year | 1979 |
Synthesis type | Total |
Number of steps | 16 (linear) |
References |
Part 1 of 1
+
+

- TMS2NLi
- (EtO)2P(O)Cl
THF
-78 °C to RT, 3 h

Pt/C,
H2
EtOAc
RT, 2.5 h, 77% (2 steps)


NH2OH,
NaOEt
MeOH
Reflux, 20 h, 89%



HCl,
(CH2OH)2
Et2O
RT, 21 h, 92%

- Li
- TMSCl
NH3, THF
-78 °C, 20 min, 86%

- MeLi
- MeI
THF
0 °C to RT, 20 h, 65%

HCl
Acetone, H2O
Reflux, 3 h


Ac2O,
HClO4
CH2Cl2
0 °C, 20 min, 64%



MeLi
Et2O
-78 °C, 4 h, 78%

POCl3
Pyr
Reflux, 2 h, 64%


LiAlH4
THF
0 °C
"No yield reported."
