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Prilezhaev Reaction

Prilezhaev Reaction

Mechanism of the Prilezhaev Reaction

Reference

Original reference Ber. Dtsch. Chem. Ges. 1909, 42, 4811.
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Sample reactions

This step is from the synthesis of Ryanodol by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure
AcOOH, NaOAc
Reaction arrow head
AcOH, H2O
RT to 80 °C, 16 h
85 % (2 steps)
Product structure

This step is from the synthesis of Ryanodol by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure
AcOOH, Na2HPO4
Reaction arrow head
DCE
4 °C, 15 h
Product structure

This step is from the synthesis of Ryanodol by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure + Reactant structure
AcOOH, Na2HPO4
Reaction arrow head
DCE
RT
Product structure + Product structure

This step is from the synthesis of Dysinosin A by Stephen Hanessian. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
RT, 2 h
Product structure

This step is from the synthesis of Chlorodysinosin A by Stephen Hanessian. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
RT, 2 h
Product structure

This step is from the synthesis of Luciduline by David A. Evans. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CHCl3
80 % (2 steps)
Product structure

This step is from the synthesis of Taxol by Samuel J. Danishefsky. Show me the full synthesis.

Reactant structure
mCPBA, NaHCO3
Reaction arrow head
CH2Cl2
RT, 11 h
80 %
Product structure

This step is from the synthesis of Taxol by Samuel J. Danishefsky. Show me the full synthesis.

Reactant structure
mCPBA, NaHCO3
Reaction arrow head
CH2Cl2
RT, 10.5 h
45 %
Product structure

This step is from the synthesis of Taxol by Paul A. Wender. Show me the full synthesis.

Reactant structure
mCPBA, Na2CO3
Reaction arrow head
CH2Cl2
-78 to -15 °C, 14 h
Product structure

This step is from the synthesis of Phyllanthocin by David R. Williams. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
10 °C to RT
89 %
Product structure

This step is from the synthesis of Gymnomitrol by Leo A. Paquette. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
74 %
Product structure

This step is from the synthesis of Paeoniflorigenin by Elias J. Corey. Show me the full synthesis.

Reactant structure
mCPBA, NaHCO3
Reaction arrow head
CH2Cl2
RT, 15 h
81 %
Product structure

This step is from the synthesis of Morphine by Larry E. Overman. Show me the full synthesis.

Reactant structure
Reagent structureCamphorsulfonic acid
Reaction arrow head
CH2Cl2
0 °C
60 %
Product structure

This step is from the synthesis of Morphine by Kathlyn A. Parker. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
0 °C
92 %
Product structure

This step is from the synthesis of Pseudolaric Acid B by Barry M. Trost. Show me the full synthesis.

Reactant structure
mCPBA, NaHCO3
Reaction arrow head
CH2Cl2
-20 °C, 30 min
Product structure

This step is from the synthesis of Longifolene by John E. McMurry. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CHCl3
0 °C to RT, ON
100 %
Product structure

This step is from the synthesis of Triquinacene by Robert B. Woodward. Show me the full synthesis.

Reactant structure
AcOOH, NaOAc
Reaction arrow head
AcOH, CH2Cl2
92 %
Product structure

This step is from the synthesis of Retigeranic Acid by Paul A. Wender. Show me the full synthesis.

Reactant structure
mCPBA, NaOAc
Reaction arrow head
CH2Cl2
RT, 24 h
Product structure

This step is from the synthesis of Asteltoxin by Stuart L. Schreiber. Show me the full synthesis.

Reactant structure
mCPBA, NaHCO3
Reaction arrow head
CH2Cl2
80 %
Product structure

This step is from the synthesis of Cyclophellitol by Ken-Ichi Sato. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
DCE
40 °C, 24 h
84 %
Product structure

This step is from the synthesis of Hirsutene by Takeshi Matsumoto. Show me the full synthesis.

Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
RT, 30 min
98 %
Product structure

This step is from the synthesis of Azadirachtin by Steven V. Ley. Show me the full synthesis.

Reactant structure
Reagent structureMMPP, NaHCO3
Sealed tube
Reaction arrow head
MeOH
110 °C, 7 d
22 % (α), 65 % (β)
Product structure

This step is from the synthesis of Hirsutene by John B. Stothers. Show me the full synthesis.

Reactant structure + Reactant structure
mCPBA
Reaction arrow head
CH2Cl2
0 °C to RT, 16 h
85 %
Product structure + Product structure
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