Synthesis of Clavukerin A

Structure of Clavukerin A

C12H18

Principal investigatorErich L. Grimm
Publication year2003
Synthesis typePartial
Number of steps 10 (linear)
References
Pure Appl. Chem. 2003, 75, 231.
Part 1 of 1
intermediate structure
NaBH4
MeOH
0 °C
"The starting material is obtained in 3 steps from (+)-limonene, see: J. Org. Chem. 1964, 29, 3740."
intermediate structure
PBr3
Et2O
0 °C
intermediate structure
PhSO2Na
DMF
RT, 15 h, 85% (3 steps)
intermediate structure
  1. Sia2BH
  2. H2O2 , H2O
THF
RT, 2.5 h
intermediate structure
MsCl
Et3N
0 °C, 60 min
intermediate structure
NaI
Acetone
65 °C, 16 h, 92% (3 steps)
See the Finkelstein Reaction
intermediate structure
NaH, Dimethyl malonate
DMF
0 to 140 °C, 17 h, 51%
intermediate structure
TMS2NLi
THF
0 °C, 89%
intermediate structure
NaBH4
MeOH
93%
intermediate structure
Na(Hg)
MeOH
0 °C, 3 h, 89%
See the Julia Olefination
intermediate structure
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