Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorR. Daniel Little
Publication year1983
Synthesis typeFormal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure
NaBH4
THF
0 °C to RT, 3.5 h, 61%
intermediate structure
i-Bu2AlH
Et2O
-20 °C, 90 min, 76%
intermediate structure
Ph3P=CH2
See the Wittig Reaction
"No yield reported."
intermediate structure
HCrO3Cl.Pyr, Celite
CH2Cl2
"No yield reported."
intermediate structure + intermediate structure
Et2NH
MeOH
5 °C to RT, 2 h, 77%
intermediate structure + intermediate structure
Et2O
0 °C, 60 min, 100%
intermediate structure
AcOH
CH2Cl2
"No yield reported."
intermediate structure
LiClO4, K3Fe(CN)6
DMF, H2O
0 °C to RT, 2 h, 55%
intermediate structure
THF
Reflux, 6 h, 63%
"Also isolated was the C6-epimer (13 % yield)."
intermediate structure
BH3.THF
THF
intermediate structure
HCrO3Cl.Pyr, Celite
CH2Cl2
61% (2 steps)
intermediate structure
NaOMe, HCO2Et
PhH
0 °C to RT, 20 h, 97%
intermediate structure
TsOH, MgSO4, n-BuSH
PhH
Reflux, 20 h, 82%
intermediate structure
KOt-Bu, MeI
t-BuOH
0 °C to reflux, 30 min, 50%
"The yield was 59% BRSM."
intermediate structure
KOH
Ethylene Glycol, H2O
Reflux, 24 h, 51%
intermediate structure
Remaining...
70% (1 step)
"See: Tetrahedron Lett. 1976, 17, 195."
intermediate structure