Synthesis of Indolizidine 223A

Structure of Indolizidine 223A

C15H29N

Principal investigatorFranklin A. Davis
Publication year2005
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Ti(OEt)4
CH2Cl2
RT, 3 h, 84%
intermediate structure + intermediate structure
TMS2NLi
Et2O
-78 °C, 3 h, 78%
"Also isolated was the C5-epimer (8 % yield)."
intermediate structure
CF3CO2H
MeOH
0 °C to RT, 2 h
intermediate structure + intermediate structure
MgSO4
CH2Cl2
RT, 2 h
intermediate structure
TsOH
PhH
RT, 40 h, 58% (3 steps)
"Also isolated was the C2-epimer (18% yield)."
intermediate structure
Na2CO3, AllylBr
EtOH
Reflux, 6 h, 91%
intermediate structure
Grubbs catalyst (1st gen.)
CH2Cl2
Reflux, 2 h
intermediate structure
H2, Pd/C
MeOH
RT, 4 h, 72% (2 steps)
intermediate structure
NaBH4
MeOH
-78 °C to RT, 2 h, 90%
intermediate structure
Pyr, PhOC(S)Cl
CH2Cl2
0 °C to RT, 24 h, 55%
intermediate structure
AIBN, n-Bu3SnH
PhH
Reflux, 4 h, 74%
intermediate structure