1583282-02-3Relevant academic research and scientific papers
Enantioselective total synthesis of pinnaic acid and halichlorine
Xu, Shu,Unabara, Daisuke,Uemura, Daisuke,Arimoto, Hirokazu
, p. 367 - 375 (2014/01/06)
The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation- cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction. Copyright
