Synthesis of Xyloketal A

Structure of Xyloketal A

C27H36O6

Principal investigatorPeter D. Wilson
Publication year2006
Synthesis typeTotal
Number of steps 8 (linear)
References
Org. Lett. 2006, 8, 1427.
Part 1 of 1
intermediate structure
  1. LDA
  2. Propargyl bromide
HMPA, THF
-78 °C, 20.5 h, 77%
intermediate structure
LiAlH4
THF
0 °C, 45 min, 73%
intermediate structure
NaNH2
Reflux, 4 h
intermediate structure
Reflux, 18 h, 72% (2 steps)
intermediate structure
Cl3CCOCl, Pyr
CH2Cl2
-78 °C to RT, 21 h, 93%
intermediate structure
NaHCO3
MeOH
Reflux, 1 h, 98%
intermediate structure
LiAlH4
Et2O
0 °C to RT, 20 min
intermediate structure + intermediate structure
MgSO4, BF3.OEt2
Et2O
-78 °C, 20 min, 63%
intermediate structure
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