Two concise total syntheses of (-)-bitungolide F.
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.
ElMarrouni
Abdelatif
A
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Joolakanti
Shyamsunder R
SR
Colon
Aude
A
Heras
Montserrat
M
Arseniyadis
Stellios
S
Cossy
Janine
J
D000475:Alkenes / Q000138:chemical synthesis*; D000478:Alkylation; D015394:Molecular Structure; D010744:Phosphoric Monoester Hydrolases / Q000037:antagonists & inhibitors; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D011753:Pyrones; C528466:bitungolide F; D010744:Phosphoric Monoester Hydrolases