Synthesis of Ammosamide B

Structure of Ammosamide B

C12H10ClN5O2

Principal investigator	Mark Cushman
Publication year	2010
Synthesis type	Total
Number of steps	9 (linear)
References	Org. Lett. 2010, 12, 3112.

Part 1 of 1

intermediate structure

NH3

Ethylene Glycol

140 °C, 3 h, 88%

intermediate structure

Boc2O, DMAP

DMF

RT, 12 h, 80%

intermediate structure

CF3CO2H

CH2Cl2

0 °C, 4 h, 90%

intermediate structure

Pd/C, H2

2 atm

EtOAc

RT, 12 h, 85%

intermediate structure

+

intermediate structure

Cu(OAc)2, TsOH

CHCl3

Reflux, 8.5 h, 50%

See the Doebner-Miller Reaction

intermediate structure

NCS

DMF

60 °C, 30 min, 75%

intermediate structure

CF3CO2H

CH2Cl2

RT, 6 h, 65%

intermediate structure

NaH, MeI

DMF

RT, 30 min, 70%

intermediate structure

NH3

H2O, THF

RT, 24 h, 80%

intermediate structure

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