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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Tarun K. Sarkar
Publication year 1990
Synthesis type Formal synthesis
Number of steps 16 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
3,4-Dihydropyran, TsOH
Et2O
Reflux, 5 h, 45%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-60 °C to RT, 50 min, 80%

See the Swern Oxidation
Chemical structure + Chemical structure
TMS2NNa
THF
-78 °C to RT, ON, 61%

See the Wittig Reaction
Chemical structure
TsOH
MeOH
Reflux, 90 min, 97%
Chemical structure
HCrO3Cl.Pyr, NaOAc
CH2Cl2
RT, 2 h, 87%
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
DME
RT, 3 h, 76%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
Sealed tube
PhMe
245 °C, 30 h, 97%

See the Ene Reaction
Chemical structure
LiAlH4
Et2O
RT to Reflux, 5 h, 90%
Chemical structure
H2Cr2O7.2Pyr
4 Å MS
AcOH, CH2Cl2
0 °C to RT, 50 min, 82%
Chemical structure
NaH, DMSO, TMSI
THF
0 °C to RT, 2 h, 61%

See the Johnson-Corey-Chaykovsky Reaction
Chemical structure
TiCl4
CH2Cl2
-78 °C, 60 min, 72%

See the Hosomi-Sakurai Reaction
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
RT, 90 min, 70%
Chemical structure
O2, PdCl2, CuCl2
DMF, H2O
RT to 57 °C, 4.5 h, 77%

See the Wacker Oxidation
Chemical structure
KOH
EtOH, H2O
55 °C, 90 min, 40%

See the Aldol Condensation
Chemical structure
H2, Pt/C
1 atm
EtOAc
RT, 60 min, 98%
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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