Synthesis of Morphine

C17H19NO3

Principal investigator	Barry M. Trost
Publication year	2002
Synthesis type	Formal
Number of steps	13 (linear)
References	J. Am. Chem. Soc. 2002, 124, 14542. Angew. Chem. Int. Ed. 2002, 41, 2795.

Part 1 of 1

Et3N, (n3-C3H3PdCl)2

CH2Cl2

RT, 8 h, 72%

See the Trost Asymmetic Allylation Alkylation

HC(OMe)3, TsOH

MeOH

50 °C, 4 h, 100%

i-Bu2AlH

PhMe

-78 °C, 60 min, 85%

DIAD, Ph3P

Et2O

-20 °C, 5 h

See the Mitsunobu Reaction

TsOH

H2O, THF

RT, 4 h, 84% (2 steps)

"98:02 er after recrystallization."

Pd(OAc)2, dppp, Ag2CO3

PhMe

107 °C, 24 h, 91%

See the Mizoroki-Heck Reaction

CBr4, Ph3P

CH2Cl2

0 °C, 10 min, 91%

See the Corey-Fuchs Reaction

Pd(PPh3)4, n-Bu3SnH

PhMe

RT, 20 min, 88%

See the Stille Coupling

Pd(OAc)2, 																	
																						dppp, 																	
																						Ag2CO3

																	PhMe															

								107 °C, 								4 h, 								65%
							
								See the Mizoroki-Heck Reaction
							
								"The yield was 74 % brsm."