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Named reactions

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Search synthesis

Hirsutene

Chemical structure of Hirsutene
C15H24
Author Kuniaki Tatsuta
Publication year 1979
Synthesis type Formal synthesis
Number of steps 20 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
Br2
THF
10 °C
Chemical structure
(CH2OH)2, TsOH
PhH
Reflux
Chemical structure
KOt-Bu
DMSO
15 °C
Chemical structure
NBS, Bz2O2
CCl4
Reflux

See the Wohl-Ziegler Reaction
Chemical structure
AgOAc
Et2O
RT, 54 % (5 steps)
Chemical structure
+
Chemical structure
Cyclohexane
RT, 2.5 d
Chemical structure
NaBH4
MeOH
Chemical structure
MeOCH2Cl, i-Pr2NEt
RT, 5 h
Chemical structure
NaOMe
MeOH
RT, 24 h, 74 % (3 steps)
Chemical structure
TsCl
Pyr
RT, 4 h, 82 %
Chemical structure
K2CO3
Sealed tube
Acetone, H2O
85 °C, 24 h, 90 %
Chemical structure
Zn, NaI
DMF, H2O
130 °C, 2 d
Chemical structure
H2SO4
Acetone, H2O
RT, 4 h, 56 % (2 steps)
Chemical structure
H2, Pd
3 atm
MeOH
Chemical structure
LiAlH4
THF
87 % (2 steps)
Chemical structure
No experimental details were reported.
Chemical structure
n-Bu3SnH, AIBN
PhH
90 %

See the Barton-McCombie Reaction
Chemical structure
H2SO4
Acetone, H2O
50 °C
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
86 % (2 steps)
Chemical structure

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Remaining...
70 % (1 step)

See: Tetrahedron Lett. 1976, 17, 195.
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