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

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

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

2012

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.

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