Synthesis of Acromelobinic Acid

C9H10N2O5

Principal investigator	Maciej Adamczyk
Publication year	2001
Synthesis type	Total
Number of steps	10 (linear)
References	Tetrahedron Asymmetry 2001, 12, 2385.

Part 1 of 1

mCPBA

CHCl3

RT, 15 h, 78%

Ac2O

Reflux, 3 h

NaOMe

MeOH

0 & deg;C, 10 min, 60% (2 steps)

Ag2CO3, MeI

CHCl3

RT, 5 d, 93%

NBS, AIBN

CCl4

Reflux, 45 min, 77%

See the Wohl-Ziegler Reaction

HMTA

AcOH, H2O

Reflux, 60 min, 34%

See the Sommelet Reaction

1,1,3,3-Tetramethylguanidine

																	THF															

								0 °C to RT, 								6 h, 								66%
							
								See the Horner-Wadsworth-Emmons Reaction
							
								"Also isolated was the E-isomer (10 % yield)."

2.5 atm

MeOH

RT, 93%

See the Noyori Asymmetric Hydrogenation

LiOH

H2O, THF

RT, 60 min

TMSI

CHCl3, MeOH

Reflux, 19 h, 88% (2 steps)

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