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Named reactions

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Ryanodol

"This paper is dedicated to Prof. Karel Wiesner on the occasion of his 60th birthday"

Chemical structure of Ryanodol
C19H30O8
Author Pierre Deslongchamps
Publication year 1979
Synthesis type Total synthesis
Number of steps 41 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
H2, PtO2
Et2O
Chemical structure
  1. O3
  2. H2, Pd/C
EtOAc
Chemical structure
(CH2OH)2, TsOH
PhH
70% (3 steps)
Chemical structure
LiH, VinylLi
THF
Chemical structure

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Part 2 of 3
Chemical structure
MeOCHCl2, TiCl4
CH2Cl2

See the Rieche Formylation
Chemical structure
BBr3
CH2Cl2
80% (2 steps)
Chemical structure
BrCH2COBr
Pyr
Chemical structure
Na2CO3
THF
Reflux, 80% (2 steps)

See the Williamson Ether Synthesis
Chemical structure
NH2NH2, KOH
Ethylene Glycol
80%

See the Wolff-Kishner Reduction
Chemical structure
NBS, NaOH
MeCN, H2O
95%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
PhH
Reflux, 60 min, 100%

See the Diels-Alder Reaction
Mixture of isomers.
Chemical structure
NaOH
THF, H2O
RT

See the Aldol Addition
Mixture of isomers.
Chemical structure
AcOH
H2O
75 °C, 2 h

Mixture of isomers.
Chemical structure
NaOH
THF
RT

See the Aldol Addition
Chemical structure
COCl2, Pyr
PhH
27% (4 steps)
Chemical structure
HC(OMe)3, TsOH
MeOH
Chemical structure
AcOOH, NaOAc
AcOH, H2O
RT to 80 °C, 16 h, 85% (2 steps)

See the Baeyer-Villiger Oxidation
See the Prilezhaev Reaction
Chemical structure
WCl6, n-BuLi
THF
-78 °C, 80%
Chemical structure
  1. O3, TsOH
  2. Me2S
EtOAc
90%

See the Aldol Addition
Chemical structure
  1. i-Pr2NLi
  2. Et3B
  3. MeI
THF
-78 to -25 °C, 3 h, 70%
Chemical structure
NaBH4
THF, MeOH
0 °C, 95%
Chemical structure
  1. NaH
  2. MeOCH2Cl
THF
80%
Chemical structure
LiAlH4
THF
95%
Chemical structure
CrO3.2Pyr
CH2Cl2
-45 to -22 °C, 60 min, 76%

See the Collins Oxidation
Chemical structure
MsCl
Pyr
0 °C, 60 min, 89%
Chemical structure
Dimsyl lithium
DMSO
RT, 30 min

See the Grob Fragmentation
Chemical structure
HBF4
H2O
0 °C, 3 h, 97% (2 steps)
Chemical structure
AcOOH, Na2HPO4
DCE
4 °C, 15 h

See the Prilezhaev Reaction
Chemical structure
NaOH
DME, H2O
RT, 5.5 h, 77% (2 steps)
Chemical structure
p-NO2BzCl
Pyr
0 °C, 25 min, 95%
Chemical structure
CrO3.2Pyr
CH2Cl2
RT, 78%

See the Collins Oxidation
Chemical structure
LiBH4
THF
-30 to -20 °C, 90 min, 73%
Chemical structure
Ac2O
Pyr
RT, 100%
Chemical structure
TsOH
PhH
Reflux
Chemical structure
  1. O3
  2. Me2S
CH2Cl2
Chemical structure
NaOAc
Ac2O
100 °C, 15 h
Chemical structure
DBN
PhH
75 °C, 2.5 h, 50% (4 steps)
Chemical structure
NaBH4
THF
0 °C, 2 h, 90%
Chemical structure
NaOH
H2O
RT, 24 h

Selectivity : 70:30
Chemical structure
+
Chemical structure
AcOOH, Na2HPO4
DCE
RT

See the Prilezhaev Reaction
Chemical structure
+
Chemical structure
Li
NH3
60% (3 steps)
Chemical structure

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