Synthesis of Indolizidine 223A

Structure of Indolizidine 223A

C15H29N

Principal investigatorDawei Ma
Publication year2005
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
n-BuLi
THF
-78 °C to RT, 6 h, 67%
intermediate structure
LiAlH4
THF
Reflux, 12 h, 90%
intermediate structure
SOCl2
CHCl3
0 °C to Reflux, 60 min
intermediate structure
H2, Pd(OH)2/C
MeOH
40 °C, 48 h, 90% (2 steps)
intermediate structure + intermediate structure
K2CO3
MeCN
Reflux, , 80%
intermediate structure
H2, PtO2
AcOH
RT, 2 h
intermediate structure
NaOEt
EtOH
Reflux, 5 h, 81% (2 steps)
intermediate structure
LiAlH4
THF
RT, 60 min, 91%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 35 min
See the Swern Oxidation
intermediate structure
TMS2NNa, Ph3P+CH3 I-
THF
-78 to 0 °C, 90 min
See the Wittig Reaction
intermediate structure
H2, Pd/C
EtOAc
RT, 2 h, 49% (3 steps)
intermediate structure