Stereospecific synthesis of beta3-amino acid derivatives from propargylic alcohols: efficient solution-phase synthesis of oligopeptides without coupling agents.
A stereospecific synthesis of beta(3)-amino acids has been accomplished starting from readily available and enantioenriched propargylic alcohols. This conversion can be effected in only three steps by selenium-mediated organic transformations of the carbon-carbon triple bond. This method is especially attractive because the reactive Se-phenyl selenocarboxylate intermediates can be trapped with the amine functionality of an amino acid derivative. Through this strategy a chain elongation at the N-terminus has been effected. The N-deprotection and repetition of the homologation with other Se-phenyl selenocarboxylate intermediates produced beta- and mixed alpha/beta-oligopeptides without the use of coupling agents.
Temperini
Andrea
A
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, via del Liceo 1, 06123 Perugia (Italy), Fax: (+39) 075-5855116.
Terlizzi
Raffaella
R
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, via del Liceo 1, 06123 Perugia (Italy), Fax: (+39) 075-5855116.
Testaferri
Lorenzo
L
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, via del Liceo 1, 06123 Perugia (Italy), Fax: (+39) 075-5855116.
Tiecco
Marcello
M
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, via del Liceo 1, 06123 Perugia (Italy), Fax: (+39) 075-5855116.
D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D000596:Amino Acids; D009842:Oligopeptides; D009942:Organometallic Compounds; D020005:Propanols; C028255:propargyl alcohol; D012643:Selenium