Synthesis of Hirsutene

C15H24
Principal investigator | Kuniaki Tatsuta |
---|---|
Publication year | 1979 |
Synthesis type | Formal |
Number of steps | 20 (linear) |
References |
Part 1 of 1
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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."
