Synthesis of Gymnomitrol

Structure of Gymnomitrol

C15H24O

Principal investigatorGeorge Büchi
Publication year1979
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
mCPBA
CH2Cl2
intermediate structure
KOH
85% (2 steps)
intermediate structure
DDQ
MeOH
0 °C, , 63%
intermediate structure + intermediate structure
SnCl4
CH2Cl2, MeNO2
-20 °C, 10 min
intermediate structure + intermediate structure
NaBH4
MeOH
-20 °C, 10 min, 10% (2 steps)
intermediate structure
H2, Pd/C
EtOAc
77%
intermediate structure
Camphorsulfonic acid, 3,4-Dihydropyran
CH2Cl2
20 °C, 60 min
intermediate structure
Ca
NH3, THF
10 min, 78% (2 steps)
intermediate structure
n-BuLi, Ph3P+CH3 Br-
DMSO, THF
80 °C, 3.5 h
See the Wittig Reaction
intermediate structure
AcOH
H2O, THF
60 °C, 7 h, 78% (2 steps)
intermediate structure