Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigatorRobert M. Coates
Publication year1979
Synthesis typeTotal
Number of steps 16 (linear)
References
J. Am. Chem. Soc. 1979, 101, 6765.
Part 1 of 1
intermediate structure
  1. TMS2NLi
  2. (EtO)2P(O)Cl
THF
-78 °C to RT, 3 h
intermediate structure
Pt/C, H2
EtOAc
RT, 2.5 h, 77% (2 steps)
intermediate structure
HCO2Et, NaH
THF
RT, 14 h, 83%
See the Claisen Condensation
intermediate structure
NH2OH, NaOEt
MeOH
Reflux, 20 h, 89%
intermediate structure + intermediate structure
PhH
Reflux, 22 h, 76%
See the Michael Addition
intermediate structure
HCl, (CH2OH)2
Et2O
RT, 21 h, 92%
intermediate structure
  1. Li
  2. TMSCl
NH3, THF
-78 °C, 20 min, 86%
intermediate structure
  1. MeLi
  2. MeI
THF
0 °C to RT, 20 h, 65%
intermediate structure
HCl
Acetone, H2O
Reflux, 3 h
intermediate structure
H2SO4, CrO3
Acetone
92% (2 steps)
See the Jones Oxidation
intermediate structure
Ac2O, HClO4
CH2Cl2
0 °C, 20 min, 64%
intermediate structure
i-Bu2AlH
THF
-78 to 0 °C, 6 h
See the Fujimoto-Belleau Reaction
intermediate structure
CrO3, H2SO4
Acetone
54% (2 steps)
See the Jones Oxidation
intermediate structure
MeLi
Et2O
-78 °C, 4 h, 78%
intermediate structure
POCl3
Pyr
Reflux, 2 h, 64%
intermediate structure + intermediate structure
LiAlH4
THF
0 °C
"No yield reported."
intermediate structure
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