Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorJanine Cossy
Publication year1987
Synthesis typeTotal
Number of steps 9 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Pd(OAc)2, P(Oi-Pr)3
PhMe
Reflux, 20 h, 60%
intermediate structure
CH2N2, Pd(OAc)2
Et2O
0 °C, 30 min, 99%
intermediate structure
H2, NaOAc, PtO2
AcOH
RT, 20 h, 82%
intermediate structure + intermediate structure
KH
DME
-70 to 0 °C, 3 h, 71%
intermediate structure
LiAlH4
Et2O
0 °C, 60 min, 90%
intermediate structure
KH
1,3-Diaminopropane
0 °C, 60 min, 86%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 4 h, 96%
intermediate structure
Et3N
MeCN
RT, 2.5 h, 58%
intermediate structure
MeMgBr, (Ph3P)2NiCl2
PhH
Reflux, 66 h, 35%
intermediate structure