Utilizing the intramolecular Fukuyama-Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design.
We report the synthesis of the novel scaffolds pyrazino[1,2-b]isoquinoline and pyrrolo[1,2-a]pyrazine displaying the somatostatin pharmacophores. Both classes of compounds contain a pyrazine heterocycle, which can be prepared in a straightforward manner utilizing an intramolecular Fukuyama-Mitsunobu reaction. As both the families derive from amino acids, they can be accessed in high optical purity.
Zapf
Christoph W
CW
Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343, USA. czapf@Princeton.edu
Del Valle
Juan R
JR
Goodman
Murray
M
D000596:Amino Acids / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D003500:Cyclization; D015195:Drug Design; D006801:Humans; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D017481:Receptors, Somatostatin / Q000378:metabolism
D000596:Amino Acids; D010455:Peptides; D017481:Receptors, Somatostatin