Synthesis of Ryanodol
C19H30O8
| Principal investigator | Pierre Deslongchamps |
|---|---|
| Publication year | 1979 |
| Synthesis type | Total |
| Number of steps | 41 (3 parts) |
| References |
Part 1 of 3
H2,
PtO2
Et2O
- O3
- H2 , Pd/C
EtOAc
(CH2OH)2,
TsOH
PhH
70% (3 steps)
LiH,
VinylLi
THF
Part 2 of 3
BBr3
CH2Cl2
80% (2 steps)
BrCH2COBr
Pyr
NaOH,
NBS
H2O, MeCN
95%
Part 3 of 3
+
+
+
+
AcOH
H2O
75 °C, 2 h
"Mixture of isomers."
Pyr,
Phosgene
PhH
27% (4 steps)
TsOH,
HC(OMe)3
MeOH
NaOAc,
AcOOH
AcOH, H2O
RT to 80 °C, 16 h, 85% (2 steps)
See the Baeyer-Villiger Oxidation
See the Prilezhaev Reaction
n-BuLi,
WCl6
THF
-78 °C, 80%
- i-Pr2NLi
- Et3B
- MeI
THF
-78 to -25 °C, 3 h, 70%
NaBH4
MeOH, THF
0 °C, 95%
- NaH
- MeOCH2Cl
THF
80%
LiAlH4
THF
95%
MsCl
Pyr
0 °C, 60 min, 89%
HBF4
H2O
0 °C, 3 h, 97% (2 steps)
NaOH
DME, H2O
RT, 5.5 h, 77% (2 steps)
p-NO2BzCl
Pyr
0 °C, 25 min, 95%
LiBH4
THF
-30 to -20 °C, 90 min, 73%
Ac2O
Pyr
RT, 100%
TsOH
PhH
Reflux
- O3
- Me2S
CH2Cl2
NaOAc
Ac2O
100 °C, 15 h
DBN
PhH
75 °C, 2.5 h, 50% (4 steps)
NaBH4
THF
0 °C, 2 h, 90%
NaOH
H2O
RT, 24 h
+
+
Li
NH3
60% (3 steps)