Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine N

Bosch, CarolineFiser, BelaGómez-Bengoa, EnriqueBradshaw, BenBonjoch i Sesé, Josep2019-02-192019-02-192015-09-251523-7060https://hdl.handle.net/2445/128419A unified strategy for the synthesis of the cisphlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, which allowed the facial selectivity of standard hydrogenation to be completely overturned. Calculations were performed to determine the mechanism, and structures for huperzines M and N are reassigned.4 p.application/pdfeng(c) American Chemical Society , 2015AlcaloidesCompostos heterocíclicsSíntesi orgànicaProductes naturalsAlkaloidsHeterocyclic compoundsOrganic synthesisNatural productsApproach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (−)-Huperzine Ninfo:eu-repo/semantics/article6666412019-02-19info:eu-repo/semantics/openAccess26406568