title: Enantioselective total synthesis of (+)-lyngbyabellin M.
abstract: Lyngbyabellin M is a non-ribosomal peptide synthetase/polyketide synthase derived metabolite isolated from the cyanobacterium M. bouillonii displaying thiazole rings and a distinct chlorinated octanoic acid chain. Its absolute configuration was proposed based on the comparison of its spectroscopic data with those of other representatives of this family of marine natural products, as well as degradation and derivatization studies. Here the first total synthesis of (+)-lyngbyabellin M is described based on the coupling of three key intermediates: two chiral thiazole moieties and an anti hydroxycarboxylic acid prepared stereoselectively via a boron enolate mediated aldol reaction directed by Masamune's chiral auxiliary.
authors.affiliation: Institute of Chemistry, University of Campinas (UNICAMP), P.O. Box 6154, CEP 13083-970 Campinas, São Paulo, Brazil. vezula@gmail.com.
authors.forename: Rodrigo V
authors.initials: RV
authors.lastname: Pirovani
authors.affiliation: Institute of Chemistry, University of Campinas (UNICAMP), P.O. Box 6154, CEP 13083-970 Campinas, São Paulo, Brazil. gilmarbrj@gmail.com.
authors.forename: Gilmar A
authors.initials: GA
authors.lastname: Brito
authors.affiliation: Institute of Chemistry, University of Campinas (UNICAMP), P.O. Box 6154, CEP 13083-970 Campinas, São Paulo, Brazil. rosicbarcelos@gmail.com.
authors.forename: Rosimeire C
authors.initials: RC
authors.lastname: Barcelos
authors.affiliation: Institute of Chemistry, University of Campinas (UNICAMP), P.O. Box 6154, CEP 13083-970 Campinas, São Paulo, Brazil. pilli@iqm.unicamp.br.
authors.forename: Ronaldo A
authors.initials: RA
authors.lastname: Pilli
mesh_terms: D000458:Cyanobacteria / Q000737:chemistry*; D008235:Lyngbya Toxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D008235:Lyngbya Toxins; D013844:Thiazoles
keywords: chiral thiazoles; lyngbyabellin M; stereoselective anti aldol; total synthesis