Rapid assembly of the polyhydroxylated beta-amino acid constituents of microsclerodermins C, D, and E.
A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.
Hjelmgaard
Thomas
T
Laboratoire de Synthèse et Etude de Systèmes d'Intérêt Biologique, SEESIB (UMR 6504 - CNRS), Université Blaise Pascal - Clermont-Ferrand 2, 24 avenue des Landais, 63177 Aubière cedex, France.
Faure
Sophie
S
Lemoine
Pascale
P
Viossat
Bernard
B
Aitken
David J
DJ
D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
D000596:Amino Acids; D007097:Imines; D010456:Peptides, Cyclic; D013452:Sulfonium Compounds; C528588:microsclerodermin C; C528589:microsclerodermin D; C486898:microsclerodermin E; C522016:sulfinimine