title: Two concise total syntheses of (-)-bitungolide F.
abstract: The enantioselective total synthesis of the dual-specificity phosphatase inhibitor (-)-bitungolide F has been achieved using two convergent routes. Both strategies feature an asymmetric boron-mediated pentenylation, a stereoselective aldol, and a hydroxyl-directed 1,3-anti-reduction in order to control the stereogenic centers at C4, C5, C9, and C11. Whereas the first total synthesis was achieved in 11 steps and 14.6% overall yield using an Evans-type asymmetric alkylation, the second was completed in 9 steps and 11.4% overall yield using a highly enantioselective organocatalytic Michael addition as a key step and a protecting group free strategy.
authors: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors: Abdelatif
authors: A
authors: ElMarrouni
authors: Shyamsunder R
authors: SR
authors: Joolakanti
authors: Aude
authors: A
authors: Colon
authors: Montserrat
authors: M
authors: Heras
authors: Stellios
authors: S
authors: Arseniyadis
authors: Janine
authors: J
authors: Cossy
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D000478:Alkylation; D015394:Molecular Structure; D010744:Phosphoric Monoester Hydrolases / Q000037:antagonists & inhibitors; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D011753:Pyrones; C528466:bitungolide F; D010744:Phosphoric Monoester Hydrolases