161117-67-5Relevant articles and documents
Strategies for the solid-phase diversification of poly-L-proline-type II peptide mimic scaffolds and peptide scaffolds through guanidinylation
Flemer, Stevenson,Wurthmann, Alexander,Mamai, Ahmed,Madalengoitia, Jose S.
, p. 7593 - 7602 (2008/12/22)
(Chemical Equation Presented) A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pmc-N′-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH2Cl2 followed by EDCI-mediated reaction of N-Pmc-N′-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.
Enantioselective total synthesis of (-)-dehydrobatzelladine C
Collins, Shawn K.,McDonald, Andrew I.,Overman, Larry E.,Rhee, Young Ho
, p. 1253 - 1255 (2007/10/03)
The oxidation of two tethered Biginelli adducts was examined as a potential key step in total syntheses of highly oxidized batzelladine and crambescidin alkaloids. Although angular hydroxyl substitution could not be introduced, dehydrogenation was readily accomplished. This latter conversion is a key step in the first total synthesis of dehydrobatzelladine C.