title: Total synthesis of etnangien.
abstract: The first total synthesis of the potent RNA-polymerase inhibitor etnangien is described, which establishes unequivocally the relative and absolute configuration of this sensitive macrolide antibiotic. Key features of the expedient and modular synthesis include stereoselective substrate-controlled boron- and tin-mediated aldol couplings to set the characteristic sequences of methyl and hydroxyl bearing stereogenic centers with high degrees of stereoselectivity and yield, an efficient Heck macrocyclization of a conformationally restricted substrate, and a late-stage introduction of the labile side chain. The convergent approach should be amenable to designed analogues.
authors: Institut für Organische Chemie, Ruprecht-Karls-Universität Heidelberg, INF 270, D-69120 Heidelberg, Germany.
authors: Pengfei
authors: P
authors: Li
authors: Jun
authors: J
authors: Li
authors: Fatih
authors: F
authors: Arikan
authors: Wiebke
authors: W
authors: Ahlbrecht
authors: Michael
authors: M
authors: Dieckmann
authors: Dirk
authors: D
authors: Menche
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors; D018942:Macrolides / Q000138:chemical synthesis*; D011090:Polyenes / Q000138:chemical synthesis*
chemical_list: D000900:Anti-Bacterial Agents; D018942:Macrolides; D011090:Polyenes; C521655:etnangien; D012321:DNA-Directed RNA Polymerases