Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide.
A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI(2)-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Wen-Ju
WJ
Bai
Stephen K
SK
Jackson
Thomas R R
TR
Pettus
D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D000458:Cyanobacteria / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D009842:Oligopeptides; D011758:Pyrroles; D011760:Pyrrolidinones; C552389:palau'imide; C009435:tetramic acid