Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorKuniaki Tatsuta
Publication year1979
Synthesis typeFormal
Number of steps 20 (linear)
References
Part 1 of 1
intermediate structure
Br2
THF
10 °C
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux
intermediate structure
KOt-Bu
DMSO
15 °C
intermediate structure
NBS, Bz2O2
CCl4
Reflux
intermediate structure
AgOAc
Et2O
RT, , 54% (5 steps)
intermediate structure + intermediate structure
Cyclohexane
RT, 2.5 d
intermediate structure
NaBH4
MeOH
intermediate structure
MeOCH2Cl, i-Pr2NEt
RT, 5 h
intermediate structure
NaOMe
MeOH
RT, 24 h, 74% (3 steps)
intermediate structure
TsCl
Pyr
RT, 4 h, 82%
intermediate structure
K2CO3
Acetone, H2O
85 °C, 24 h, 90%
intermediate structure
Zn, NaI
DMF, H2O
130 °C, 2 d
intermediate structure
H2SO4
Acetone, H2O
RT, 4 h, 56% (2 steps)
intermediate structure
H2, Pd
MeOH
intermediate structure
LiAlH4
THF
87% (2 steps)
intermediate structure
"No experimental details were reported."
intermediate structure
n-Bu3SnH, AIBN
PhH
90%
intermediate structure
H2SO4
Acetone, H2O
50 °C
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
86% (2 steps)
intermediate structure
Remaining...
70% (1 step)
"See: <i>Tetrahedron Lett. 1976, 17, 195."
intermediate structure