Synthesis of Nominine

C20H27NO

Principal investigator	David Y. Gin
Publication year	2006
Synthesis type	Total
Number of steps	18 (3 parts)
References	J. Am. Chem. Soc. 2006, 128, 8734.

Part 1 of 3

Et2AlCN
n-Bu4N+ Ph3SiF2-
Tf2O

PhH

0 °C to RT, 19.5 h, 81%

See the Michael Addition

i-Bu2AlH

PhMe

0 °C, 30 min, 92%

Pd(PPh3)4, Cu(CN)2

DMF

60 °C, 25 min, 85%

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Part 2 of 3

t-BuLi

Et2O

-23 °C, 4.5 h, 52%

See the Weinreb Ketone Synthesis

NaN3

Acetone

RT, 38 h, 95%

AcCl

MeOH

RT, 5 min, 99%

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Part 3 of 3

n-Bu3P, NaBH(OAc)3

CH2Cl2

RT, 17 h, 79%

See the Wittig Reaction

CF3CO2H

CH2Cl2

0 °C, 3 h, 93%

Sealed tube

																	THF															

								180 °C, 								16 h, 								20%
							
								See the Huisgen Cycloaddition
							
								"Also isolated was 70 % of a regioisomer which could be thermally equilibrated to the desired product."

NaBH4

EtOH

RT, 90 min

SOCl2

CH2Cl2

50 °C, 2.5 h

n-Bu3SnH, AIBN

PhH

80 °C, 105 min, 68% (3 steps)

i-Bu2AlH

PhMe

0 °C, 100 min, 85%

Ph3P+CH3 Br-, n-BuLi

THF

RT, 95 min, 96%

See the Wittig Reaction

Na

																	i-PrOH, 																	NH3, 																	THF															

								-78 °C, 								4 h, 								97%
							
								See the Birch Reduction
							
								"Acidic quench."

Pyrrolidine

MeOH

60 °C, 4.5 h, 78%

See the Diels-Alder Reaction

Ph3P+CH3 Br-, n-BuLi

THF

70 °C, 15 h, 77%

See the Wittig Reaction

SeO2, t-BuOOH

CH2Cl2

RT, 70 min, 66%

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