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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Daniel D. Sternbach
Publication year 1990
Synthesis type Total synthesis
Number of steps 22 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
HC(OEt)3, TsOH
EtOH
Reflux, 6 h, 95%
Chemical structure
  1. O3
  2. Ph3P
CH2Cl2
-78 °C to RT, ON, 100%
Chemical structure + Chemical structure
PhH
RT to Reflux, 6 h, 81%

See the Wittig Reaction
Chemical structure
LiAlH4
Et2O
0 °C, 6 h, 99%
Chemical structure
HCl
THF, H2O
RT, 25 min, 100%
Chemical structure + Chemical structure
Pyrrolidine, Na2S2O4
MeOH
RT, 24-36 h, 99%
Chemical structure
LiAlH4
THF
RT, 6 h, 93%
Chemical structure
Mesitylene
Reflux, 24 h, 70%

See the Diels-Alder Reaction
Chemical structure
CrO3, H2SO4
Acetone, H2O
0 °C, 60 min, 97%

See the Jones Oxidation
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C to RT, 99%
Chemical structure
Ac2O, Et3N, DMAP
CH2Cl2
RT, 4 h, 90%
Chemical structure
CrO3, H2SO4
Acetone, H2O
RT, 45 min, 95%

See the Jones Oxidation
Chemical structure
(COCl)2, DMF
PhH
RT, 2 h
Chemical structure
Reagent structure
t-BuSH, DMAP
PhMe
Reflux, 45 min, 82% (2 steps)

See the Barton Decarboxylation
Chemical structure
Et3N
MeOH, H2O
RT, 60 min, 95%
Chemical structure
Ph3P+CH3 Br-, TMS2NK
THF
0 °C to RT, 30 min, 86%

See the Wittig Reaction
Chemical structure
(COCl)2, NaH
PhH
RT, 4 h
Chemical structure
Me2CuLi
Et2O
-78 to 0 °C, 60 min, 97% (2 steps)
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
-78 °C to RT, 80%
Chemical structure
KOH, n-Bu4N+ OH-
THF, Et2O
Reflux, ON, 97%

See the Aldol Condensation
Chemical structure
H2, PtO2
1 atm
EtOAc
RT, 20 min, 100%
Chemical structure
Ph3P+CH3 Br-, KH
PhH, t-BuOH
RT to Reflux, 6 h, 93%

See the Wittig Reaction
Chemical structure

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