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Named reactions

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Indolizidine 223A

Chemical structure of Indolizidine_223A
C15H29N
Author Franklin A. Davis
Publication year 2005
Synthesis type Total synthesis
Number of steps 11 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
Ti(OEt)4
CH2Cl2
RT, 3 h, 84%
Chemical structure + Chemical structure
TMS2NLi
Et2O
-78 °C, 3 h, 78%

See the Mannich Reaction
Also isolated was the C5-epimer (8 % yield).
Chemical structure
CF3CO2H
MeOH
0 °C to RT, 2 h
Chemical structure + Chemical structure
MgSO4
CH2Cl2
RT, 2 h
Chemical structure
TsOH
PhH
RT, 40 h, 58% (3 steps)

See the Mannich Reaction
Also isolated was the C2-epimer (18% yield).
Chemical structure
AllylBr, Na2CO3
EtOH
Reflux, 6 h, 91%
Chemical structure
Grubbs catalyst (1st gen.)
CH2Cl2
Reflux, 2 h

See the Olefin Metathesis
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, 4 h, 72% (2 steps)
Chemical structure
NaBH4
MeOH
-78 °C to RT, 2 h, 90%
Chemical structure
PhOC(S)Cl, Pyr
CH2Cl2
0 °C to RT, 24 h, 55%
Chemical structure
n-Bu3SnH, AIBN
PhH
Reflux, 4 h, 74%

See the Barton-McCombie Reaction
Chemical structure

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