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Named reactions

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Search synthesis

Epolactaene

Chemical structure of Epolactaene
C21H27NO6
Author Yujiro Hayashi
Publication year 2002
Synthesis type Total synthesis
Number of steps 20 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
PhH
90 °C, 90 min, 98%

See the Wittig Reaction
Chemical structure
TBSCl, Imidazole
CH2Cl2, DMF
RT, 20 min, 99%
Chemical structure
i-Bu2AlH
CH2Cl2
0 °C, 60 min
Chemical structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 90 min, 94% (2 steps)

See the Parikh-Doering Oxidation
Chemical structure + Chemical structure
NaH
THF
0 °C to RT, 60 min, 96%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
  1. i-Pr2NLi
  2. MeCHO
THF, HMPA
-78 °C, 4.5 h, 96%

See the Aldol Addition
Chemical structure
MsCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 90 min
Chemical structure
DABCO ®
MeOH
100 °C, 5 d, 86% (2 steps)
Chemical structure
n-Bu4N+ F-
THF
0 °C, 3 h, 100%
Chemical structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 90 min, 100%

See the Parikh-Doering Oxidation
Chemical structure + Chemical structure
n-BuLi
DME
0 °C to RT, 40 min, 100%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
n-BuLi, MeCN
THF
-88 to -78 °C, 60 min, 93%

See the Claisen Condensation
Chemical structure
CF3CO2H
CH2Cl2
0 °C to RT, 20 min
Chemical structure
CH2N2
Et2O
-78 °C, 92% (2 steps)
Chemical structure + Chemical structure
(CH2NH2)2.2AcOH
PhH
RT, 2 h

See the Knoevenagel Condensation
Chemical structure
Ph3COOH, n-BuLi
THF
-78 °C, 2 h

See the Michael Addition
Chemical structure
NH4F, AcOH
THF, H2O
RT, 90 min
Chemical structure
SiO2
EtOAc, Hexane(s)
Chemical structure
NH3
MeOH, H2O
0 °C, 30 min, 22% (5 steps)
Chemical structure
Pyr.SO3, DMSO, Et3N
CH2Cl2
0 °C, 2 h, 78%

See the Parikh-Doering Oxidation
Chemical structure

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