Synthesis of Twistane

Structure of Twistane

C10H16

Principal investigatorPierre Deslongchamps
Publication year1967
Synthesis typeTotal
Number of steps 7 (linear)
References
Part 1 of 1
intermediate structure
HC(OEt)3, TsOH
EtOH
-20 to 0 °C, 60 min, 65%
intermediate structure
Li
NH3, THF, EtOH
-33 °C, 60 min, 99%
intermediate structure
MsCl, Pyr
CH2Cl2
-10 °C, 24 h
intermediate structure
(CO2H)2
Et2O, H2O
RT, 2 h, 59% (2 steps)
intermediate structure
NaH
Dioxane
Reflux, 5 h, 85%
intermediate structure
(CH2SH)2, BF3.OEt2
AcOH
RT, 16 h, 100%
intermediate structure
Ni (Raney)
EtOH
Reflux, 5 h, 70%
intermediate structure