title: Enantioselective total synthesis of (+)-obtusenyne.
abstract: A total synthesis of the laurencia metabolite (+)-obtusenyne has been completed. The key steps include a Sharpless kinetic resolution and an asymmetric glycolate alkylation to establish the stereogenic centers adjacent to the ether linkage and a ring-closing metathesis reaction to construct the nine-membered ether without the aid of a cyclic conformational constraint. The synthesis was completed in 20 linear steps from commercially available 1,5-hexadiene-3-ol.
authors.affiliation: Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina, NC, USA. crimmins@email.enc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Mark T
authors.initials: MT
authors.lastname: Powell
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D000461:Rhodophyta / Q000737:chemistry
chemical_list: D000480:Alkynes; D004988:Ethers, Cyclic; C476642:obtusenyne