Stéphanie Desvergnes1, Sandrine Py, Yannick Vallée. 1. LEDSS, UMR 5616 CNRS Institut de Chimie Moléculaire de Grenoble - FR 2607 Université Joseph Fourier, B.P. 53, 38041 Grenoble, France.
Abstract
[reaction: see text] A concise total synthesis of (+)-hyacinthacine A(2), a polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastereoselective reductive coupling of a L-xylose-derived cyclic nitrone with ethyl acrylate allowed the assembly of the bicyclic core of the target molecule, by way of a tandem formation of the C-C and C-N bonds. The method opens a novel, short, and general route for the synthesis of other pyrrolizidine alkaloids.
[reaction: see text] A concise total synthesis of (+)-hyacinthacine A(2), a n class="Chemical">polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastereoselective reductive coupling of a L-xylose-derived cyclic nitrone with ethyl acrylate allowed the assembly of the bicyclic core of the target molecule, by way of a tandem formation of the C-C and C-N bonds. The method opens a novel, short, and general route for the synthesis of other pyrrolizidine alkaloids.
Authors: Lívia Dikošová; Barbora Otočková; Tomáš Malatinský; Jana Doháňošová; Mária Kopáčová; Anna Ďurinová; Lucie Smutná; František Trejtnar; Róbert Fischer Journal: RSC Adv Date: 2021-09-24 Impact factor: 4.036