A general strategy for construction of both 2,6-cis- and 2,6-trans-disubstituted tetrahydropyrans: Substrate-controlled asymmetric total synthesis of (+)-scanlonenyne

Journal Article

(Chemical Equation Presented) A synthetic three-ring circus: The asymmetric total synthesis of (+)-scanlonenyne includes a sequential epimerization and intramolecular hetero-Michael addition for the construction of pyrano-γ-lactones (see scheme; DBU: 1,8-diazabicyclo[5.4.0]undec-7-ene), a highly efficient one-carbon homologation/bromination strategy, and a Weinreb ketone synthesis/cross-metathesis protocol for the elaboration of a sensitive side chain. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Full Text

Duke Authors

Cited Authors

  • Lee, H; Kim, KW; Park, J; Kim, H; Kim, S; Kim, D; Hu, X; Yang, W; Hong, J

Published Date

  • 2008

Published In

Volume / Issue

  • 47 / 22

Start / End Page

  • 4200 - 4203

PubMed ID

  • 18435525

International Standard Serial Number (ISSN)

  • 1433-7851

Digital Object Identifier (DOI)

  • 10.1002/anie.200705663