Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigatorJohn B. Stothers
Publication year1984
Synthesis typeFormal
Number of steps 13 (linear)
References
Can. J. Chem. 1984, 62, 2521.
Part 1 of 1
intermediate structure
HCO2H
Reflux, 4 h
intermediate structure
KOH
EtOH
Reflux, 8 h
intermediate structure
Na2Cr2O7, H2SO4
Et2O, H2O
RT, 2.5 h, 72% (3 steps)
See the Jones Oxidation
"Mixture of positional isomers."
intermediate structure
  1. i-Pr2NLi
  2. TMSCl , Et3N
THF
-78 °C, 95%
intermediate structure
Zn-Ag, CH2I2
Et2O
RT, 18 h, 85%
See the Simmons-Smith Reaction
intermediate structure
NaOH
H2O, MeOH
0 °C, 24 h, 87%
intermediate structure
MeI, NaNH2
Et2O
Reflux, 21 h, 83%
intermediate structure
KOt-Bu
Sealed tube
t-BuOH
205 °C, 6.5 d, 80%
intermediate structure
NH2NH2.H2O, KOH
Sealed tube
Diethylene glycol
182 °C, 2.5 d, 90%
See the Wolff-Kishner Reduction
intermediate structure
mCPBA
CH2Cl2
0 °C to RT, 16 h, 85%
See the Prilezhaev Reaction
intermediate structure + intermediate structure
LiAlH4
Et2O
Reflux, ON, 99%
intermediate structure + intermediate structure
CrO3, H2SO4
Acetone, H2O
RT, 28%
See the Jones Oxidation
intermediate structure
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Remaining...
14% (5 step)
"See: J. Am. Chem. Soc. 1981, 103, 2744 and Tetrahedron Lett. 1976, 17, 195."
intermediate structure