Synthesis of Nupharamine

C15H25NO2

Principal investigator	José Barluenga
Publication year	1999
Synthesis type	Total
Number of steps	12 (linear)
References	J. Org. Chem. 1999, 64, 3736. Chem. Eur. J. 1996, 2, 805.

Part 1 of 1

ZnCl2

THF

-80 °C to RT, 16 h, 51%

See the Diels-Alder Reaction

Et3N, Triphosgene

THF

0 °C, 15 min, 95%

TMS2NLi
Comins' reagent

THF

-80 °C, 3 h, 67%

"The yield was 96 % brsm."

H2, PtO2

1 atm

EtOH

RT, 6-8 h, 89%

KOt-Bu

THF

0 °C, 30 min, 95%

TBSCl, Imidazole

MeCN

RT, 4 h, 67%

ClCO2Bn, K2CO3

MeCN

RT, 4 h, 99%

HCl

H2O, THF

RT, 30 min, 88%

																																							(COCl)2
																											, 
																																																				DMSO
																											, 
																																																				Et3N
																																				
																																							Ph3P=CHCO2Et
																																				
																	CH2Cl2															

								-65 °C to RT, 								5 h								
							
								See the Swern Oxidation
							
								See the Wittig Reaction

Pd/C, H2

1 atm

EtOH

RT, 3.5 h, 85%

MeLi

THF

-70 °C, 15 min, 77%

Pd, HCO2NH4

MeOH

RT, 14 h, 99%

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