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Open AccessArticle

Enantioselective Total Synthesis of (+)-Lyngbyabellin M

Institute of Chemistry, University of Campinas (UNICAMP), P.O. Box 6154, CEP 13083-970 Campinas, São Paulo, Brazil
Author to whom correspondence should be addressed.
Academic Editor: Orazio Taglialatela-Scafati
Mar. Drugs 2015, 13(6), 3309-3324;
Received: 9 February 2015 / Accepted: 17 April 2015 / Published: 27 May 2015
PDF [866 KB, uploaded 27 May 2015]


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. View Full-Text
Keywords: lyngbyabellin M; total synthesis; chiral thiazoles; stereoselective anti aldol lyngbyabellin M; total synthesis; chiral thiazoles; stereoselective anti aldol

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Pirovani, R.V.; Brito, G.A.; Barcelos, R.C.; Pilli, R.A. Enantioselective Total Synthesis of (+)-Lyngbyabellin M. Mar. Drugs 2015, 13, 3309-3324.

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