Synthesis of Strychnine

C21H22N2O2

Principal investigator	Christopher D. Vanderwal
Publication year	2011
Synthesis type	Formal
Number of steps	9 (3 parts)
References	Chem. Sci. 2011, 2, 649.

Part 1 of 3

AllylNH2

RT, 44 h, 100%

								
																	EtOH															

								RT to 80 °C, 								3.5 h, 								81%
							
								See the Zincke Reaction
							
								"The yield was 100 % brsm."

KOt-Bu

Sealed tube

THF

80 °C, 3.5 h, 64%

See the Diels-Alder Reaction

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Part 2 of 3

Me2SiH(OEt), [Cp*Ru(MeCN)3]PF6

Acetone

0 °C to RT, 2.5 h

Et3N, MsCl, LiBr

THF

-25 °C to RT, 5 h

See the Finkelstein Reaction

MeMgBr

Et2O

-78 °C, 35 min, 47% (3 steps)

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Part 3 of 3

i-Pr2NEt, Pd(PPh3)4

CHCl3, MeCN

0 °C, 3.5 h, 69%

TMS2NNa, 																	
																						CuBr.Me2S

																	NMP															

								0 to 65 °C, 								95 min, 								10%
							
								See the Michael Addition
							
								See the Brook Rearrangement

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Remaining...

70% (1 step)

"See: Chem. Ind. 1953, 245."