text: The synthesis of ring II was accomplished with a Fischer indole synthesis using phenylhydrazine 1 and acetophenone derivative acetoveratrone 2 (catalyst polyphosphoric acid) to give the 2-veratrylindole 3. The veratryl group not only blocks the 2-position for further electrophilic substitution but will also become part of the strychnine skeleton. A Mannich reaction with formaldehyde and dimethylamine) produced gramine 4. Alkylation with iodomethane gave an intermediate quaternary ammonium salt which reacted with sodium cyanide in a nucleophilic substitution to nitrile 5 and then in a reduction with lithium aluminium hydride to tryptamine 6. Amine-carbonyl condensation with ethyl glyoxylate give the imine 7. The reaction of this imine with TsCl in pyridine to the ring-closed N-tosyl compound 8 was described by Woodward as a concerted nucleophilic enamine attack and formally a Pictet–Spengler reaction. This compound should form as a diastereomeric pair but only one compound was found although which one was not investigated. Finally the newly formed double bond was reduced by sodium borohydride to indoline 9 with the C8 hydrogen atom approaching from the least hindered side (this proton is removed later on in the sequence and is of no importance).