Synthesis of Hirsutene

C15H24
Principal investigator | John B. Stothers |
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Publication year | 1984 |
Synthesis type | Formal |
Number of steps | 13 (linear) |
References |
Part 1 of 1
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HCO2H
Reflux, 4 h

KOH
EtOH
Reflux, 8 h

Na2Cr2O7,
H2SO4
Et2O, H2O
RT, 2.5 h, 72% (3 steps)
See the Jones Oxidation
"Mixture of positional isomers."

- i-Pr2NLi
- TMSCl , Et3N
THF
-78 °C, 95%


NaOH
H2O, MeOH
0 °C, 24 h, 87%

MeI,
NaNH2
Et2O
Reflux, 21 h, 83%

KOt-Bu
Sealed tube
t-BuOH
205 °C, 6.5 d, 80%




LiAlH4
Et2O
Reflux, ON, 99%



Remaining...
14% (5 step)
"See: J. Am. Chem. Soc. 1981, 103, 2744 and Tetrahedron Lett. 1976, 17, 195."
