Towards enantioselective synthesis of tryptophan-derived alkaloids.
Tryptamine was subjected to a series of reactions with derivatives of L-Ala, L-Val that ended with final diketopiperazines 9 and 10, having (R) configuration on the newly created, via 1,4-chirality transfer, stereogenic center. On the other hand, when L-Pro was used the opposite chirality sense was formed at this position.
Siwicka
Aleksandra
A
Faculty of Chemistry, Warsaw University, Pasteur St. 1, 02-093, Warsaw, Poland.
Zawadzka
Anna
A
Wojtasiewicz
Krystyna
K
Maurin
Jan K
JK
Leniewski
Andrzej
A
Czarnocki
Zbigniew
Z
D000596:Amino Acids / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D000596:Amino Acids; D026121:Indole Alkaloids; D014364:Tryptophan