Synthesis of Ammosamide B

Structure of Ammosamide B

C12H10ClN5O2

Principal investigator	William Fenical
Publication year	2010
Synthesis type	Total
Number of steps	17 (linear)
References	J. Am. Chem. Soc. 2010, 132, 2528.

Part 1 of 1

intermediate structure

H2SO4, HNO3

H2O

0 °C, 90 min, 58%

intermediate structure

t-BuNH2

Dioxane

100 °C, ON, 87%

intermediate structure

NaH, MeI

DMF

0 °C to RT, 45 min

intermediate structure

CF3CO2H

CH2Cl2

RT, 30 min, 92% (2 steps)

intermediate structure

+

intermediate structure

CH2Cl2

3.5 h, 86%

See the Wittig Reaction

intermediate structure

CF3CO2H

100 °C, ON

intermediate structure

HNO3, H2SO4

H2O

RT, ON

intermediate structure

POCl3

100 °C, ON, 85% (3 steps)

intermediate structure

HI

H2O, MeCN

RT, ON

intermediate structure

(CF3CO)2O

Pyr

0 °C, 4 min, 74% (2 steps)

intermediate structure

CuCN

Pyr

80 °C, 2 h

See the Rosenmund-von Braun Reaction

intermediate structure

H2SO4

MeOH

60 °C, ON

intermediate structure

KOH

MeOH

50 °C, 4 h

intermediate structure

H2SO4

MeOH

60 °C, 60 min

See the Fischer-Speier Esterification

intermediate structure

SOCl2

hν

RT, 45 min

intermediate structure

(CF3CO)2O

Pyr

RT, 3 h, 8% (6 steps)

intermediate structure

Mg3N2

MeOH

0 to 80 °C, ON, 100%

intermediate structure

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