Synthesis of Strychnine

C21H22N2O2
Principal investigator | David W. C. MacMillan |
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Publication year | 2011 |
Synthesis type | Total |
Number of steps | 12 (linear) |
References |
Part 1 of 1
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NaH,
(4-MeOPh)CH2Cl
DMF
0 °C to RT, 35 min, 94%

SeO2
Dioxane , H2O
100 °C, 5 h, 87%

TMS2NK,
18-Crown-6,
(EtO)2P(O)CH2SeMe
THF
-78 °C to RT, 90 min, 81%
See the Horner-Wadsworth-Emmons Reaction



(Ph3P)3RhCl
PhMe, PhCN
120 °C, 5.5 h, 86%

MeOH,
Phosgene,
Et3N
PhMe
-45 °C to RT, 3 h, 88%

CF3CO2H,
i-Bu2AlH
CH2Cl2, MeOH
-78 °C to RT, 3 h, 81%


DBU,
K2CO3
DMF
RT, 50 min, 84%

i-Bu2AlH
CH2Cl2
-78 °C, 2 h, 91%


PhSH
CF3CO2H
45 °C, 13 h, 66%

