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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
TBSOTf, Et3N
CH2Cl2
-78 °C, 60 min
-78 °C, 60 min
i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 92 % (2 steps)
-78 °C, 2 h, 92 % (2 steps)
Ph3P, i-Pr2NEt
80 °C, 24 h, 91 %
+ 
n-Bu4N+ F-
THF
0 °C to RT, 3 h, 87 %
0 °C to RT, 3 h, 87 %
+ 
t-BuLi
Et2O
-78 °C, 3.5 h, 87 %
-78 °C, 3.5 h, 87 %
HCrO3Cl.Pyr
CH2Cl2
RT, 3 h, 89 %
RT, 3 h, 89 %
LiBHEt3
THF
-78 °C, 30 min
-78 °C, 30 min
TBSOTf, Et3N
CH2Cl2
-78 °C, 2 h, 93 % (2 steps)
-78 °C, 2 h, 93 % (2 steps)
i-Bu2AlH
CH2Cl2
-78 °C, 2 h
-78 °C, 2 h
Methyl propynoate, n-BuLi
THF
-78 °C, 60 min
-78 °C, 60 min
H2, (Ph3P)3RhCl
PhH
66 °C, 3 h, 95 %
66 °C, 3 h, 95 %
Pyr.HF
THF
RT, 3 h, 91 %
RT, 3 h, 91 %
H2, Pd/C
THF
RT, 2 h, 93 %
RT, 2 h, 93 %
Comins' reagent, TMS2NK
THF
-78 °C, 3.5 h, 92 %
-78 °C, 3.5 h, 92 %
O2, P(OEt)3, K2CO3
DMF
60 °C, 80 h, 66 %
The yield was 92 % brsm.
60 °C, 80 h, 66 %
The yield was 92 % brsm.
