Synthesis of Hirsutene
C15H24
| Principal investigator | Duy H. Hua |
|---|---|
| Publication year | 1985 |
| Synthesis type | Total |
| Number of steps | 16 (linear) |
| References |
Part 1 of 1
+
+
+
Zn
AcOH
RT, 10 h, 95%
TiCl4
AcOH
RT, 20 min, 86%
(CH2OH)2,
TsOH
Dean-Stark
PhH
Reflux, 6 h, 95%
mCPBA
CH2Cl2
-20 to 0 °C, 5 h, 95%
DBN
PhMe
Reflux, 10 h, 90%
CrO3.2Pyr
CH2Cl2
RT, 24 h, 85%
+
CuI.Me2S,
Li
Et2O
-30 °C to RT, 2.5 h, 85%
See the Michael Addition
"Also isolated was the C6'-epimer (5 % yield)."
n-Bu4N+ F-
THF
RT, 15 h, 97%
TsCl
Pyr
RT, 20 h, 99%
NaH
DME
Reflux, 5 h, 90%
NaBH4
MeOH
-10 °C, 60 min, 95%
Et3N,
i-PrSO2Cl
Et2O
0 °C to RT, 3 h, 93%
LiBHEt3
PhMe
90 °C, 24 h, 72%
TsOH
H2O, MeOH, THF
RT, 60 min, 90%