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Hirsutene
"This paper is dedicated to Professor Peter Yates on the occasion of his 60th birthday"
| Author | John B. Stothers |
|---|---|
| Publication year | 1984 |
| Synthesis type | Formal synthesis |
| Number of steps | 13 (linear) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 1
Reflux, 4 h
KOH
EtOH
Reflux, 8 h
Reflux, 8 h
Na2Cr2O7, H2SO4
Et2O, H2O
RT, 2.5 h, 72 % (3 steps)
Selectivity : 70:30
See the Jones Oxidation
Mixture of positional isomers.
RT, 2.5 h, 72 % (3 steps)
Selectivity : 70:30
See the Jones Oxidation
Mixture of positional isomers.
i-Pr2NLi, TMSCl, Et3N
THF
-78 °C, 95 %
-78 °C, 95 %
NaOH
MeOH, H2O
0 °C, 24 h, 87 %
0 °C, 24 h, 87 %
NaNH2, MeI
Et2O
Reflux, 21 h, 83 %
Reflux, 21 h, 83 %
KOt-Bu
Sealed tube
t-BuOH
205 °C, 6.5 d, 80 %
Selectivity : 50:50
Sealed tube
205 °C, 6.5 d, 80 %
Selectivity : 50:50
+ 
NH2NH2.H2O, KOH
Sealed tube
Diethylene glycol
182 °C, 2.5 d, 90 %
Selectivity : 50:50
See the Wolff-Kishner Reduction
Sealed tube
182 °C, 2.5 d, 90 %
Selectivity : 50:50
See the Wolff-Kishner Reduction
+ 
+ 
LiAlH4
Et2O
Reflux, ON, 99 %
Selectivity : 50:50
Reflux, ON, 99 %
Selectivity : 50:50
+ 
Remaining...
Tetrahedron Lett. 1976, 17, 195.
