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
MeNO2, CH2Cl2
-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
3,4-Dihydropyran, Camphorsulfonic acid
CH2Cl2
20 °C, 60 min
intermediate structure
Ca
THF, NH3
10 min, 78% (2 steps)
intermediate structure
Ph3P+CH3 Br-, n-BuLi
THF, DMSO
80 °C, 3.5 h
See the Wittig Reaction
intermediate structure
AcOH
THF, H2O
60 °C, 7 h, 78% (2 steps)
intermediate structure