124128-12-7Relevant academic research and scientific papers
Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types
Node, Manabu,Nagasawa, Hideko,Fuji, Kaoru
, p. 517 - 521 (1990)
Expeditious enantioselective syntheses of (+)-quebrachamine (6), (-)-aspidospermidine (7), (+)-demethoxyaspidospermine (8), and (-)-eburnamonine (9) were accomplished starting from (S)-lactone 1.The syntheses also complete formal, total syntheses of 12 other indole alkaloids of the Aspidosperma and Hunteria types.The key step in the synthesis of (+)-quebrachamine (6) was the Pictet-Spengler condensation of chiral C9 unit 10, derived from 1, with tryptamine.Another C9 unit (15) was also prepared from 1 and utilized for the syntheses of three other alkaloids, 7, 8, and 9.
