Next Article in Journal
Influence of Core Oligosaccharide of Lipopolysaccharide to Outer Membrane Behavior of Escherichia coli
Previous Article in Journal
Production of Chondroitin Sulphate from Head, Skeleton and Fins of Scyliorhinus canicula By-Products by Combination of Enzymatic, Chemical Precipitation and Ultrafiltration Methodologies
Article Menu

Export Article

Open AccessArticle
Mar. Drugs 2015, 13(6), 3309-3324; doi:10.3390/md13063309

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
Received: 9 February 2015 / Accepted: 17 April 2015 / Published: 27 May 2015
View Full-Text   |   Download PDF [866 KB, uploaded 27 May 2015]   |  

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. View Full-Text
Keywords: lyngbyabellin M; total synthesis; chiral thiazoles; stereoselective anti aldol lyngbyabellin M; total synthesis; chiral thiazoles; stereoselective anti aldol
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top