Synthesis of Reserpine

C33H40N2O9

Principal investigator	Gilbert Stork
Publication year	2005
Synthesis type	Total
Number of steps	12 (linear)
References	J. Am. Chem. Soc. 2005, 127, 16255.

Part 1 of 1

n-BuLi
Me2SiHCl

Et2O

-25 °C to Reflux, 8 h, 85%

Co2(CO)8

PhH

45-47 °C, 2 h, 33%

i-Pr2NLi

THF

-78 to 0 °C, 3 h, 88%

See the Diels-Alder Reaction

n-Bu4N+ F-

THF

RT, 2 min, 84%

Pd/C, H2

1 atm

EtOAc

RT, 30 h, 98%

TsCl, Pyr, DMAP

CH2Cl2

55 °C, 10 h, 72%

Na2HPO4, 																	
																						mCPBA

																	CH2Cl2															

								RT, 								15 h, 								61%
							
								See the Baeyer-Villiger Oxidation
							
								See the Fleming-Tamao Oxidation

CaSO4, Ag2O, MeI

RT, 20 h, 96%

i-Bu2AlH

Et2O, THF

-78 °C, 30 min, 84%

MgSO4, KCN

MeCN

RT, 70 min, 87%

HCl

H2O, THF

RT, 30 h, 92%

See the Pictet-Spengler Reaction

Pyr

RT, 4 d, 95%

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