Synthesis of Indolizidine 223A

Structure of Indolizidine 223A

C15H29N

Principal investigator	Dawei Ma
Publication year	2005
Synthesis type	Total
Number of steps	11 (linear)
References	Org. Lett. 2005, 7, 705.

Part 1 of 1

intermediate structure

+

intermediate structure

n-BuLi

THF

-78 °C to RT, 6 h, 67%

See the Michael Addition

intermediate structure

LiAlH4

THF

Reflux, 12 h, 90%

intermediate structure

SOCl2

CHCl3

0 °C to Reflux, 60 min

intermediate structure

Pd(OH)2/C, H2

50 atm

MeOH

40 °C, 48 h, 90% (2 steps)

intermediate structure

+

intermediate structure

K2CO3

4 Å MS

MeCN

Reflux, 80%

intermediate structure

PtO2, H2

1 atm

AcOH

RT, 2 h

intermediate structure

NaOEt

EtOH

Reflux, 5 h, 81% (2 steps)

intermediate structure

LiAlH4

THF

RT, 60 min, 91%

intermediate structure

Et3N, DMSO, (COCl)2

CH2Cl2

-78 °C to RT, 35 min

See the Swern Oxidation

intermediate structure

Ph3P+CH3 I-, TMS2NNa

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

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