Synthesis of Alkaloid 251F

C16H29NO

Principal investigator	Jeffrey Aubé
Publication year	2002
Synthesis type	Total
Number of steps	10 (linear)
References	J. Am. Chem. Soc. 2002, 124, 9974.

Part 1 of 1

NHMeOMe.HCl, BOP reagent

CH2Cl2, Et3N

RT, 24.5 h, 95%

VinylMgBr

THF

0 °C, 60 min, 95%

See the Weinreb Ketone Synthesis

C2H4, Grubbs catalyst (1st gen.)

1 atm

CH2Cl2

RT, 12 h, 93%

See the Olefin Metathesis

MeLi, 																	
																						CuI

																	THF															

								0 °C to RT, 								45 min, 								60%
							
								See the Aldol Condensation
							
								See the Michael Addition

EtOH, NH3, THF

-78 °C, 10 min, 54%

See the Birch Reduction

Zn(N3)2.2Pyr, Ph3P, DEAD

RT, 12 h, 100%

See the Mitsunobu Reaction

O3
Me2S

CH2Cl2

-78 °C to RT, 24 h, 70%

NaBH4

EtOH

0 °C, 78%

TfOH

CH2Cl2

0 °C, 6 h, 79%

See the Schmidt Reaction

LiAlH4

Et2O

0 °C, 20 min, 86%

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