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Named reactions

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Search synthesis

Yohimbine

Chemical structure of Yohimbine
C21H26N2O3
Author Eugene E. van Tamelen
Publication year 1958
Synthesis type Formal synthesis
Number of steps 21 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
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Chemical structure
PhH
RT, 2-3 weeks, 93%

See the Diels-Alder Reaction
Chemical structure
Zn
AcOH
30-50 °C, 40 min, 93%
Chemical structure
ClCH2CO2Et, KOt-Bu
PhH, t-BuOH
RT, ON, 81%

See the Darzens Condensation
Chemical structure
NaOH
H2O
RT to 100 °C, 45 min, 87%
Chemical structure
Cu
Diethylene glycol
155-160 °C, 2 h, 76%
Chemical structure
AgNO3, KOH
EtOH, H2O
RT, 12 h, 38%

See the Tollens Oxidation
Chemical structure
(COCl)2, Pyr
Et2O
RT, 8 h
Chemical structure + Chemical structure
Pyr
CHCl3
5 °C, 10 h, 75% (2 steps)
Chemical structure
OsO4, Pyr
THF, Et2O
-78 °C, 2.5 h, 56%

Single, unidentified cis-isomer. Also isolated was the other cis-diastereoisomer (11 % yield).
Chemical structure
H2, PtO2
EtOH
RT, 60 min, 85%
Chemical structure
NaIO4, H3PO4
Acetone, H2O
60-70 °C, 20 min, 60%

See the Pictet-Spengler Reaction
Chemical structure
TsOH
MeOH
RT, 3 d, 77%
Chemical structure
LiAlH4
THF
Reflux, 4 h, 76%
Chemical structure
HCl
H2O
100 °C, 3 h, 82%
Chemical structure
Ac2O
Pyr
RT, ON
Chemical structure
285-295 °C, 5 min, 71% (2 steps)
Chemical structure
OsO4, Pyr
THF
-78 °C, 7 h, 37%
Chemical structure
NaIO4
MeOH, H2O
0 °C, 2 h, 81%
Chemical structure
CrO3, H2SO4
MeOH, Acetone, H2O
0 °C, 30 min, 16%

See the Jones Oxidation
Chemical structure

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Remaining...
65% (2 steps)

See : Acta Chim. Scand. 1956, 10, 1414.
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