The synthesis of tyromycin A and that of the non-natural lower homologue, involving as featuring stepsa transition metal catalyzed atom transfer radical cyclization and a functional rearrangement of thepolyhalogenated 2-pyrrolidinones thus obtained, are described. Both routes use 10-undecenoic acid,a renewable source from castor oil, as starting material for the preparation of the pivotal intermediatesa,a,a0,a0-tetrachlorodicarboxylic acids.
A new synthetic route to Tyromycin A and its analogue from renewable resources / Roncaglia, Fabrizio; C. V., Stevens; Ghelfi, Franco; M., Van der Steen; Pattarozzi, Mariella; L., De Buyck. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 65:7(2009), pp. 1481-1487. [10.1016/j.tet.2008.11.091]
A new synthetic route to Tyromycin A and its analogue from renewable resources
RONCAGLIA, Fabrizio;GHELFI, Franco;PATTAROZZI, Mariella;
2009
Abstract
The synthesis of tyromycin A and that of the non-natural lower homologue, involving as featuring stepsa transition metal catalyzed atom transfer radical cyclization and a functional rearrangement of thepolyhalogenated 2-pyrrolidinones thus obtained, are described. Both routes use 10-undecenoic acid,a renewable source from castor oil, as starting material for the preparation of the pivotal intermediatesa,a,a0,a0-tetrachlorodicarboxylic acids.
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