Enantioselective total synthesis of (+)-obtusenyne.
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.
Crimmins
Michael T
MT
Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina, NC, USA. crimmins@email.enc.edu
Powell
Mark T
MT
D000480:Alkynes / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D000461:Rhodophyta / Q000737:chemistry
D000480:Alkynes; D004988:Ethers, Cyclic; C476642:obtusenyne