Synthesis of Hirsutene
C15H24
Principal investigator | Kuniaki Tatsuta |
---|---|
Publication year | 1979 |
Synthesis type | Formal |
Number of steps | 20 (linear) |
References |
Part 1 of 1
+
Br2
THF
10 °C
(CH2OH)2,
TsOH
PhH
Reflux
KOt-Bu
DMSO
15 °C
AgOAc
Et2O
RT, 54% (5 steps)
hν
Cyclohexane
RT, 2.5 d
NaBH4
MeOH
i-Pr2NEt,
MeOCH2Cl
RT, 5 h
NaOMe
MeOH
RT, 24 h, 74% (3 steps)
TsCl
Pyr
RT, 4 h, 82%
K2CO3
Sealed tube
Acetone, H2O
85 °C, 24 h, 90%
Zn,
NaI
DMF, H2O
130 °C, 2 d
H2SO4
Acetone, H2O
RT, 4 h, 56% (2 steps)
H2,
Pd
3 atm
MeOH
LiAlH4
THF
87% (2 steps)
"No experimental details were reported."
H2SO4
Acetone, H2O
50 °C
HCrO3Cl.Pyr
CH2Cl2
86% (2 steps)
Remaining...
70% (1 step)
"See: <i>Tetrahedron Lett. 1976, 17, 195."