Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Lanier, ML; Park, H; Mukherjee, P; Timmerman, JC; Ribeiro, AA; Widenhoefer, RA; Hong, J

Published Date

  • May 3, 2017

Published In

Volume / Issue

  • 23 / 30

Start / End Page

  • 7180 - 7184

PubMed ID

  • 28393406

Pubmed Central ID

  • PMC5653968

Electronic International Standard Serial Number (EISSN)

  • 1521-3765

International Standard Serial Number (ISSN)

  • 0947-6539

Digital Object Identifier (DOI)

  • 10.1002/chem.201700499


  • eng