Synthesis of Reserpine

C33H40N2O9

Principal investigator	Robert B. Woodward
Publication year	1956
Synthesis type	Total
Number of steps	28 (3 parts)
References	J. Am. Chem. Soc. 1956, 78, 2023. J. Am. Chem. Soc. 1956, 78, 2657. Tetrahedron 1958, 2, 1.

Part 1 of 3

NaNO2 , HCl
CuSO4 , NH2OH.HCl , NaOAc , (CH2O)n

H2O

0-5 °C

NH4FeSO4.12H2O

H2O

40 min, 63% (2 steps)

NH4OAc, MeNO2

AcOH

Reflux, 2 h, 65%

See the Henry Reaction

Pd/C, H2

3.4 atm

AcOH, EtOAc, EtOH

RT, 55%

See the Leimgruber-Batcho Indole Synthesis

(COCl)2

Et2O

0 °C, 30 min, 90%

NH3

H2O

40-50 °C, 30 min, 90%

LiAlH4

THF

Reflux, ON, 63%

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Part 2 of 3

								
																	PhH															

								Reflux, 								10 h, 								8%
							
								See the Diels-Alder Reaction
							
								""[This method was not] investigated extensively with a view to determining optimum conditions.""