Asymmetric synthesis of the highly methylated tryptophan portion of the hemiasterlin tripeptides.
[reaction: see text] The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.
Reddy
Ranga
R
Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Jaquith
James B
JB
Neelagiri
Venugopal Rao
VR
Saleh-Hanna
Sherine
S
Durst
Tony
T
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D008745:Methylation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D000970:Antineoplastic Agents; D009842:Oligopeptides; C467070:hemiasterlin; D014364:Tryptophan