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Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation. 2017
Megan L Lanier, and
Hyeri Park, and
Paramita Mukherjee, and
Jacob C Timmerman, and
Anthony A Ribeiro, and
Ross A Widenhoefer, and
Jiyong Hong
Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α'-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.
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