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Named reactions

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Caribenol A

Chemical structure of Caribenol_A
C19H26O3
Author Zhen Yang
Publication year 2010
Synthesis type Total synthesis
Number of steps 24 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
TBSOTf, Et3N
CH2Cl2
-78 °C, 60 min
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 92 % (2 steps)
Chemical structure
I2, Ph3P, Imidazole
MeCN, Et2O
0 °C to RT, 70 min, 89 %

See the Appel Reaction
Chemical structure
Ph3P, i-Pr2NEt
80 °C, 24 h, 91 %
Chemical structure
+
Chemical structure
TMS2NNa
THF
-78 °C to RT, 4 h, 92 %

See the Wittig Reaction
Chemical structure
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87 %
Chemical structure
I2, Ph3P, Imidazole
MeCN, Et2O
0 °C to RT, 2 h, 85 %

See the Appel Reaction
Chemical structure
+
Chemical structure
t-BuLi
Et2O
-78 °C, 3.5 h, 87 %
Chemical structure
HCrO3Cl.Pyr
CH2Cl2
RT, 3 h, 89 %
Chemical structure
LiBHEt3
THF
-78 °C, 30 min
Chemical structure
TBSOTf, Et3N
CH2Cl2
-78 °C, 2 h, 93 % (2 steps)
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
RT, 2 h, 80 % (2 steps)

See the Dess-Martin Oxidation
Chemical structure
Methyl propynoate, n-BuLi
THF
-78 °C, 60 min
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
RT, 2 h, 87 % (2 steps)

See the Dess-Martin Oxidation
Chemical structure
BHT
PhMe
120 °C, 24 h, 92 %

See the Diels-Alder Reaction
Chemical structure
H2, (Ph3P)3RhCl
PhH
66 °C, 3 h, 95 %
Chemical structure
Pyr.HF
THF
RT, 3 h, 91 %
Chemical structure
NaBH4, CeCl3.7H2O
EtOH
0 °C, 30 min, 92 %

See the Luche Reduction
Chemical structure
n-Pr4N+ RuO4-, NMO
4Å MS
CH2Cl2
RT, 90 min, 91 %

See the Ley-Griffith Oxidation
Chemical structure
H2, Pd/C
THF
RT, 2 h, 93 %
Chemical structure
  1. TMS2NK
  2. Comins' reagent
THF
-78 °C, 3.5 h, 92 %
Chemical structure
Me2Zn, Pd(PPh3)4
THF
RT, 60 min, 84 %

See the Negishi Coupling
Chemical structure
O2, P(OEt)3, K2CO3
DMF
60 °C, 80 h, 66 %

The yield was 92 % brsm.
Chemical structure

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