111154-23-5Relevant academic research and scientific papers
Enantiocontrolled synthesis of a chiral building block via diastereoselective ring-closing metathesis
Murakami, Yuri,Shindo, Mitsuru,Shishido, Kozo
, p. 664 - 666 (2005)
An enantiocontrolled construction of a chiral building block, which had been converted into an indole alkaloid (-)-eburnamonine, has been accomplished using a diastereoselective ring-closing metathesis for the construction of the quaternary stereogenic ce
Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types
Node, Manabu,Nagasawa, Hideko,Fuji, Kaoru
, p. 517 - 521 (2007/10/02)
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.
