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Named reactions

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Search synthesis

Hirsutene

"This paper is dedicated to Professor Peter Yates on the occasion of his 60th birthday"

Chemical structure of Hirsutene
C15H24
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
Chemical structure
HCO2H
Reflux, 4 h
Chemical structure
KOH
EtOH
Reflux, 8 h
Chemical structure
Na2Cr2O7, H2SO4
Et2O, H2O
RT, 2.5 h, 72% (3 steps)

Selectivity : 70:30
See the Jones Oxidation
Mixture of positional isomers.
Chemical structure
  1. i-Pr2NLi
  2. TMSCl, Et3N
THF
-78 °C, 95%
Chemical structure
Zn-Ag, CH2I2
Et2O
RT, 18 h, 85%

See the Simmons-Smith Reaction
Chemical structure
NaOH
MeOH, H2O
0 °C, 24 h, 87%
Chemical structure
NaNH2, MeI
Et2O
Reflux, 21 h, 83%
Chemical structure
KOt-Bu
Sealed tube
t-BuOH
205 °C, 6.5 d, 80%

Selectivity : 50:50
Chemical structure
NH2NH2.H2O, KOH
Sealed tube
Diethylene glycol
182 °C, 2.5 d, 90%

Selectivity : 50:50
See the Wolff-Kishner Reduction
Chemical structure
mCPBA
CH2Cl2
0 °C to RT, 16 h, 85%

Selectivity : 50:50
See the Prilezhaev Reaction
Chemical structure
+
Chemical structure
LiAlH4
Et2O
Reflux, ON, 99%

Selectivity : 50:50
Chemical structure
+
Chemical structure
CrO3, H2SO4
Acetone, H2O
RT, 28%

See the Jones Oxidation
Chemical structure

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Remaining...
14% (5 step)

See: J. Am. Chem. Soc. 1981, 103, 2744 and Tetrahedron Lett. 1976, 17, 195.
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