1245071-00-4Relevant academic research and scientific papers
Two concise total syntheses of (-)-bitungolide F
Elmarrouni, Abdelatif,Joolakanti, Shyamsunder R.,Colon, Aude,Heras, Montserrat,Arseniyadis, Stellios,Cossy, Janine
, p. 4074 - 4077 (2010)
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.
