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Named reactions

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Search synthesis

Gymnomitrol

Chemical structure of Gymnomitrol
C15H24O
Author Robert M. Coates
Publication year 1979
Synthesis type Total synthesis
Number of steps 16 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
  1. TMS2NLi
  2. (EtO)2P(O)Cl
THF
-78 °C to RT, 3 h
Chemical structure
H2, Pt/C
EtOAc
RT, 2.5 h, 77% (2 steps)
Chemical structure
NaH, HCO2Et
THF
RT, 14 h, 83%

See the Claisen Condensation
Chemical structure
NH2OH, NaOEt
MeOH
Reflux, 20 h, 89%
Chemical structure + Chemical structure
PhH
Reflux, 22 h, 76%

See the Michael Addition
Chemical structure
(CH2OH)2, HCl
Et2O
RT, 21 h, 92%
Chemical structure
  1. Li
  2. TMSCl
THF, NH3
-78 °C, 20 min, 86%
Chemical structure
  1. MeLi
  2. MeI
THF
0 °C to RT, 20 h, 65%
Chemical structure
HCl
Acetone, H2O
Reflux, 3 h
Chemical structure
CrO3, H2SO4
Acetone
92% (2 steps)

See the Jones Oxidation
Chemical structure
Ac2O, HClO4
CH2Cl2
0 °C, 20 min, 64%
Chemical structure
i-Bu2AlH
THF
-78 to 0 °C, 6 h

See the Fujimoto-Belleau Reaction
Chemical structure
CrO3, H2SO4
Acetone
54% (2 steps)

See the Jones Oxidation
Chemical structure
MeLi
Et2O
-78 °C, 4 h, 78%
Chemical structure
POCl3
Pyr
Reflux, 2 h, 64%

Selectivity : 50:50
Chemical structure
+
Chemical structure
LiAlH4
THF
0 °C

No yield reported.
Chemical structure

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