Stereoselective synthesis of tetrahydropyrans through tandem and organocatalytic oxa-Michael reactions: Synthesis of the tetrahydropyran cores of ent-(+)-sorangicin A

Published

Journal Article

Tandem and organocatalytic oxa-Michael reactions of α,β- unsaturated aldehydes were explored for the stereoselective synthesis of structurally complex tetrahydropyrans. Thestereoselective synthesis of 2,6-trans-tetrahydropyrans, which are thermodynamically unfavorable, was accomplished through a reagent-controlled, organocatalytic oxa-Michael reaction. A temperature-dependent configurational switch allowed the preparation of both 2,3-trans-2,6-trans-and 2,3-cis-2,6-cis-tetrahydropyrans from a common substrate. This switch was then used to synthesize the precursors of the C21-C29 and C30-C37 fragments of ent-(+)-sorangicin A. The tandem and organocatalytic oxa-Michael reactions of α,β-unsaturated aldehydes were explored and applied to the stereoselective synthesis of structurally complex tetrahydropyrans. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Full Text

Duke Authors

Cited Authors

  • Lee, K; Kim, H; Hong, J

Published Date

  • February 1, 2012

Published In

Start / End Page

  • 1025 - 1032

Electronic International Standard Serial Number (EISSN)

  • 1099-0690

International Standard Serial Number (ISSN)

  • 1434-193X

Digital Object Identifier (DOI)

  • 10.1002/ejoc.201101549

Citation Source

  • Scopus