Synthesis of Indolizidine 223A
C15H29N
| Principal investigator | Franklin A. Davis |
|---|---|
| Publication year | 2005 |
| Synthesis type | Total |
| Number of steps | 11 (linear) |
| References |
Part 1 of 1
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Ti(OEt)4
CH2Cl2
RT, 3 h, 84%
+
TMS2NLi
Et2O
-78 °C, 3 h, 78%
See the Mannich Reaction
"Also isolated was the C5-epimer (8 % yield)."
CF3CO2H
MeOH
0 °C to RT, 2 h
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MgSO4
CH2Cl2
RT, 2 h
TsOH
PhH
RT, 40 h, 58% (3 steps)
See the Mannich Reaction
"Also isolated was the C2-epimer (18% yield)."
AllylBr,
Na2CO3
EtOH
Reflux, 6 h, 91%
Pd/C,
H2
1 atm
MeOH
RT, 4 h, 72% (2 steps)
NaBH4
MeOH
-78 °C to RT, 2 h, 90%
PhOC(S)Cl,
Pyr
CH2Cl2
0 °C to RT, 24 h, 55%