Synthesis of Caribenol A

Structure of Caribenol A

C19H26O3

Principal investigatorZhen Yang
Publication year2010
Synthesis typeTotal
Number of steps 24 (linear)
References
J. Am. Chem. Soc. 2010, 132, 13608.
Part 1 of 1
intermediate structure
TBSOTf, Et3N
CH2Cl2
-78 °C, 60 min
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 92% (2 steps)
intermediate structure
Ph3P, Imidazole, I2
Et2O, MeCN
0 °C to RT, 70 min, 89%
See the Appel Reaction
intermediate structure
Ph3P, i-Pr2NEt
80 °C, 24 h, 91%
intermediate structure + intermediate structure
TMS2NNa
THF
-78 °C to RT, 4 h, 92%
See the Wittig Reaction
intermediate structure
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87%
intermediate structure
I2, Ph3P, Imidazole
Et2O, MeCN
0 °C to RT, 2 h, 85%
See the Appel Reaction
intermediate structure + intermediate structure
t-BuLi
Et2O
-78 °C, 3.5 h, 87%
intermediate structure
HCrO3Cl.Pyr
CH2Cl2
RT, 3 h, 89%
intermediate structure
LiBHEt3
THF
-78 °C, 30 min
intermediate structure
TBSOTf, Et3N
CH2Cl2
-78 °C, 2 h, 93% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
intermediate structure
NaHCO3, Dess-Martin Periodinane
CH2Cl2
RT, 2 h, 80% (2 steps)
See the Dess-Martin Oxidation
intermediate structure
Methyl propynoate, n-BuLi
THF
-78 °C, 60 min
intermediate structure
NaHCO3, Dess-Martin Periodinane
CH2Cl2
RT, 2 h, 87% (2 steps)
See the Dess-Martin Oxidation
intermediate structure
BHT
PhMe
120 °C, 24 h, 92%
See the Diels-Alder Reaction
intermediate structure
(Ph3P)3RhCl, H2
PhH
66 °C, 3 h, 95%
intermediate structure
Pyr.HF
THF
RT, 3 h, 91%
intermediate structure
NaBH4, CeCl3.7H2O
EtOH
0 °C, 30 min, 92%
See the Luche Reduction
intermediate structure
n-Pr4N+ RuO4-, NMO
4Å MS
CH2Cl2
RT, 90 min, 91%
See the Ley-Griffith Oxidation
intermediate structure
Pd/C, H2
THF
RT, 2 h, 93%
intermediate structure
  1. TMS2NK
  2. Comins' reagent
THF
-78 °C, 3.5 h, 92%
intermediate structure
Me2Zn, Pd(PPh3)4
THF
RT, 60 min, 84%
See the Negishi Coupling
intermediate structure
O2, K2CO3, P(OEt)3
DMF
60 °C, 80 h, 66%
"The yield was 92 % brsm."
intermediate structure
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