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.
Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA 92093-0343, USA. czapf@Princeton.edu
Christoph W
CW
Zapf
Juan R
JR
Del Valle
Murray
M
Goodman
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