Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigatorLeo A. Paquette
Publication year1979
Synthesis typeTotal
Number of steps 13 (linear)
References
J. Org. Chem. 1979, 44, 3731.
Part 1 of 1
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux, 95%
intermediate structure
NH2NH2, KOH
Ethylene Glycol
Reflux, 82%
See the Wolff-Kishner Reduction
intermediate structure
"No experimental details were reported for this step."
intermediate structure
PhNHMe.TFA, (CH2O)3
Dioxane
45%
See the Claisen-Schmidt Condensation
"The yield was 90 % brsm."
intermediate structure + intermediate structure
  1. CuBr.Me2S
  2. MeI
HMPA
66%
See the Michael Addition
intermediate structure
mCPBA
CH2Cl2
74%
See the Prilezhaev Reaction
intermediate structure
H2SO4
MeOH
Reflux, 24 h, 74%
"Also isolated was the desired aldol product (22% yield, see the next two steps)."
intermediate structure + intermediate structure
H2O
AcOH
74%
intermediate structure
KOH
MeOH
2.5 d, 26%
See the Aldol Addition
"The yield was 61 % brsm."
intermediate structure
H2SO4, CrO3
Acetone
89%
See the Jones Oxidation
intermediate structure
MeLi
-78 °C, 70%
intermediate structure
POCl3
Pyr
Reflux, 2 h, 70%
intermediate structure + intermediate structure
LiAlH4
THF
0 °C, 45%
intermediate structure
Report an error in this part