An Expedient Enantioselective Strategy for the Oxatetracyclic Core of Platensimycin
- 10 May 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (12) , 2417-2419
Abstract
An enantioselective route for the synthesis of oxatetracyclic core of platensimycin is reported for the first time using a 5-exo-trig cyclization followed by intramolecular etherification as key reactions. The requisite dienynone for the radical cyclization is synthesized in eight steps from the Wieland−Miescher ketone employing a Claisen rearrangement.Keywords
This publication has 8 references indexed in Scilit:
- Formal synthesis of (±)-platensimycinChemical Communications, 2007
- Graphical Abstract: Angew. Chem. Int. Ed. 1‐2/2007Angewandte Chemie International Edition, 2006
- Platensimycin, a New Antibiotic and “Superbug Challenger” from NatureChemMedChem, 2006
- Platensimycin is a selective FabF inhibitor with potent antibiotic propertiesNature, 2006
- Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl CompoundsSynthetic Communications, 1989
- Stoichiometric reduction of molecular nitrogen by iron complexesJournal of the American Chemical Society, 1970
- Cycloheptatrienes from the Solvolysis of 1,4-Dihydrobenzyl p-Toluenesulfonates1Journal of the American Chemical Society, 1961
- Über Umlagerung von Phenol‐allyläthern in C‐Allyl‐phenoleEuropean Journal of Inorganic Chemistry, 1912