Synthesis of Strychnofoline

C30H34N4O2

Principal investigator	Erick M. Carreira
Publication year	2002
Synthesis type	Total
Number of steps	22 (3 parts)
References	J. Am. Chem. Soc. 2002, 124, 14826.

Part 1 of 3

BnBr, NaH

DMF

-78 °C to RT, 65 min, 72%

NH2NH2

EtOH

Reflux, 12 h, 90%

See the Wolff-Kishner Reduction

BBr3

CH2Cl2

-78 to 0 °C, 5 h, 92%

TBSCl, Imidazole

DMF

RT, 3 h, 88%

Br(CH2)2Br, NaH

DMF

0 °C, 1 h, 86%

BnBr, NaH

DMF

-45 to 0 °C, 95 min, 87%

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Part 2 of 3

TMS2NLi, PhSeCl

THF

-78, 2 h

H2O2

EtOAc, H2O

0 °C to RT, 1h, 80%

CuBr.Me2S, AllylMgBr, TMSCl

THF

-78 °C, 2 h, 75%

See the Michael Addition

i-Bu2AlH

THF

-78 °C, 2 h

HCl

CH2Cl2, H2O

RT, 5 min, 90% (2 steps)

Et3N, TMSOTf

CH2Cl2

-78 to -20 °C, 2 h, 100%

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Part 3 of 3

MgI2

Sealed Tube

THF

80 °C, 16 h, 55%

OsO4

Dioxane , H2O, t-BuOH

RT, 4 h

NaIO4

Dioxane , H2O, t-BuOH

RT, 2 h, 86% (2 steps)

TsOH, HC(OMe)3

MeOH

RT, ON, 93 %

n-Bu4N+ F-

THF

0 °C, 5 h, 86%

IBX

DMSO

RT, 12 h, 88%

Ph3P+CH3 Br-, KOt-Bu

THF

0 °C to RT, 2 h, 87%

See the Wittig Reaction

HCl

Acetone, H2O

RT, 12 h, 94%

AcOH

																	PhMe															

								80 °C, 								2 h, 								26%
							
								See the Pictet-Spengler Reaction
							
								"Also isolated, 38 % isomer"

NH3, t-BuOH, THF

-78 to -45 °C, 15 min, 82%

See the Birch Reduction

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