Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigatorSteven C. Welch
Publication year1979
Synthesis typeTotal
Number of steps 16 (linear)
References
J. Am. Chem. Soc. 1979, 101, 6768.
Part 1 of 1
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 °C to RT, 5 h, 79%
intermediate structure
Hg(OAc)2
H2O, HCO2H
RT, 91%
intermediate structure
KOH
EtOH
Reflux, 84%
See the Aldol Condensation
intermediate structure
  1. Me2CuLi
  2. AllylCl
HMPA, THF
-78 °C to RT
See the Michael Addition
See the Williamson Ether Synthesis
intermediate structure
HCl
H2O
74% (2 steps)
See the Claisen Rearrangement
intermediate structure
  1. NaH
  2. MeI
DME
64%
intermediate structure
  1. Sia2BH
  2. H2O , H2O2 , NaOH
THF
80%
intermediate structure
H2SO4, CrO3
Acetone, H2O
See the Jones Oxidation
intermediate structure
CH2N2
Et2O
84% (2 steps)
intermediate structure
  1. TMS2NLi
  2. TBSCl
Hexane(s), HMPA, THF
Reflux, 2.5 h
See the Dieckmann Condensation
intermediate structure
TBSCl, P(NMe2)3
0 °C, 65% (2 steps)
intermediate structure
NaBH4
EtOH
0 °C to RT, 6 h, 87%
intermediate structure
POCl3, 2-Methoxypropene
RT, 16 h
intermediate structure
n-Bu4N+ F-
THF
RT, 10 h, 74% (2 steps)
intermediate structure
Ph3P=CH2
DMSO
75 °C, 16 h
See the Wittig Reaction
intermediate structure
HCl
H2O, MeOH
RT, 30 min, 87% (2 steps)
intermediate structure
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