Clarifying the structure of granadaene: total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry

Miguel Paradas; Rocío Jurado; Ali Haidour; Javier Rodríguez Granger; Antonio Sampedro Martínez; Manuel de la Rosa Fraile; Rafael Robles; José Justicia; Juan M Cuerva

doi:10.1016/j.bmc.2012.09.017

Clarifying the structure of granadaene: total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry

Bioorg Med Chem. 2012 Nov 15;20(22):6655-61. doi: 10.1016/j.bmc.2012.09.017. Epub 2012 Sep 19.

Authors

Miguel Paradas¹, Rocío Jurado, Ali Haidour, Javier Rodríguez Granger, Antonio Sampedro Martínez, Manuel de la Rosa Fraile, Rafael Robles, José Justicia, Juan M Cuerva

Affiliation

¹ Department of Organic Chemistry, Faculty of Sciences, University of Granada, C. U. Fuentenueva s/n, Granada, Spain.

PMID: 23043725
DOI: 10.1016/j.bmc.2012.09.017

Abstract

Streptococcus agalactiae is an important agent in the infection of neonates in the first world. One of the most extended methods for its identification is based on the detection of a characteristic red pigment in the patient samples, named [12]-granadaene (1). In this article, we present a modular and flexible approach to simple analogues of this ornithine rhamno-polyene 1 and the elucidation of the most important features of its structure: the absolute configuration at C-27, the stereochemistry of the anomeric center and the link of the amino acid ornithine to the rest of the structure.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Molecular Conformation
Ornithine / analogs & derivatives*
Ornithine / chemical synthesis
Ornithine / chemistry
Polyenes / chemical synthesis
Polyenes / chemistry*
Stereoisomerism
Streptococcus agalactiae / chemistry*

Substances

(12)-granadaene
Polyenes
Ornithine