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Named reactions

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Search synthesis

Doliculide

Chemical structure of Doliculide
C27H41IN2O6
Author Arun K. Ghosh
Publication year 2001
Synthesis type Total synthesis
Number of steps 40 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
i-Bu2AlH
CH2Cl2
0 °C, 30 min, 85%
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 4 h, 84%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 93%
Chemical structure
Reagent structure
Et2Zn, CH2I2
CH2Cl2, DME
-15 °C, 8 h, 99%

See the Charette Asymmetric Cyclopropanation
Chemical structure
Ph3P, I2, Imidazole
CH2Cl2
RT, 60 min, 80%

See the Appel Reaction
Chemical structure
n-BuLi, (CH2NMe2)2
4 Å MS
Et2O
-78 °C to RT, 30 min, 90%
Chemical structure
  1. 9-BBN
  2. H2O2, NaOH, H2O
THF
0 °C to RT, 4 h, 80%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h

See the Swern Oxidation
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 4 h, 80% (2 steps)

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 90%
Chemical structure
Reagent structure
Et2Zn, CH2I2
CH2Cl2, DME
-15 °C, 8 h, 96%

Selectivity : 96:04 dr
See the Charette Asymmetric Cyclopropanation
Chemical structure
Ph3P, I2, Imidazole
CH2Cl2
RT, 60 min

See the Appel Reaction
Chemical structure
n-BuLi, (CH2NMe2)2
4 Å MS
Et2O
-78 °C to RT, 30 min, 74% (2 steps)
Chemical structure
  1. O3
  2. Ph3P
CH2Cl2
-78 °C to RT, 4 h
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C to RT, 4 h, 60% (2 steps)

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 90%
Chemical structure
Ti(Oi-Pr)4, (-)-DET, t-BuOOH
4 Å MS
CH2Cl2
-23 °C, 20.5 h, 90%

See the Sharpless Epoxidation
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h

See the Swern Oxidation
Chemical structure + Chemical structure
PhH
80 °C, 15 h, 81% (2 steps)

See the Wittig Reaction
Chemical structure
Pd2(dba)3.CHCl3, n-Bu3P, HCO2H, Et3N
Dioxane
RT, 10 h, 90%
Chemical structure
TBSOTf, Et3N
CH2Cl2
0 °C, 15 min
Chemical structure
i-Bu2AlH
CH2Cl2
-40 °C, 30 min, 80% (2 steps)
Chemical structure
Ti(Oi-Pr)4, (+)-DET, t-BuOOH
4 Å MS
CH2Cl2
-23 °C, 20.5 h, 91%

See the Sharpless Asymmetric Dihydroxylation
Chemical structure
MsCl, Et3N, DMAP
CH2Cl2
-78 to 0 °C, 2 h
Chemical structure
NaI
MEK
85 °C, 15 h

See the Finkelstein Reaction
Chemical structure
n-BuLi, (CH2NMe2)2
4 Å MS
Et2O
-78 °C to RT, 30 min, 84% (3 steps)
Chemical structure
H2, Pd/C
1 atm
THF
RT, 6 h, 84%
Chemical structure
n-Pr4N+ RuO4-, NMO
4 Å MS
CH2Cl2
RT, 60 min

See the Ley-Griffith Oxidation
Chemical structure
NaClO2, 2-Methyl-2-butene, NaH2PO4
t-BuOH, H2O
RT, ON

See the Pinnick-Lindgren Oxidation
Chemical structure
Boc2O, DMAP
t-BuOH
30 °C, 15 h, 57% (3 steps)
Chemical structure

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Part 2 of 3
Chemical structure
TIPSCl, Imidazole
DMF
0 °C to RT, 2 h, 98%
Chemical structure
NaH, MeI
DMF, THF
60 °C, 20 h
Chemical structure
CF3CO2H
CH2Cl2
0 °C to RT, 3 h, 50% (2 steps)
Chemical structure + Chemical structure
EDC, HOBt
DMF
0 °C to RT, 20 h, 90%
Chemical structure
LiOH
THF, H2O
0 °C, 60 min, 100%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
DCC, DMAP
CH2Cl2
-20 °C, 20 h, 98%

See the Steglich Esterification
Chemical structure
CF3CO2H
CH2Cl2
0 °C to RT, 3 h
Chemical structure
BOP reagent, DMAP
CH2Cl2
0 °C to RT, 24 h, 82% (2 steps)
Chemical structure
NH3
MeOH, H2O
RT, 60 min, 88%
Chemical structure
n-Bu4N+ F-
THF
0 °C, 15 min, 98%
Chemical structure

Report an error in this part

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