Synthesis of Caribenol A

Structure of Caribenol A

C19H26O3

Principal investigatorZhen Yang
Publication year2010
Synthesis typeTotal
Number of steps 24 (linear)
References
Part 1 of 1
intermediate structure
Et3N, TBSOTf
CH2Cl2
-78 °C, 60 min
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 92% (2 steps)
intermediate structure
I2, Imidazole, Ph3P
Et2O, MeCN
0 °C to RT, 70 min, 89%
See the Appel Reaction
intermediate structure
i-Pr2NEt, Ph3P
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, Imidazole, Ph3P
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
Et3N, TBSOTf
CH2Cl2
-78 °C, 2 h, 93% (2 steps)
intermediate structure
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
intermediate structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
RT, 2 h, 80% (2 steps)
intermediate structure
n-BuLi, Methyl propynoate
THF
-78 °C, 60 min
intermediate structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
RT, 2 h, 87% (2 steps)
intermediate structure
BHT
PhMe
120 °C, 24 h, 92%
intermediate structure
H2, (Ph3P)3RhCl
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
NMO, n-Pr4N+ RuO4-
CH2Cl2
RT, 90 min, 91%
intermediate structure
H2, Pd/C
THF
RT, 2 h, 93%
intermediate structure
  1. TMS2NK
  2. Comins' reagent
THF
-78 °C, 3.5 h, 92%
intermediate structure
Pd(PPh3)4, Me2Zn
THF
RT, 60 min, 84%
intermediate structure
K2CO3, O2, P(OEt)3
DMF
60 °C, 80 h, 66%
"The yield was 92 % brsm."
intermediate structure