Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.

Journal Article (Journal Article)

The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of α,β-unsaturated ketone catalyzed by primary diamine for the synthesis of the 2,6-trans-tetrahydropyran embedded in psymberin.

Full Text

Duke Authors

Cited Authors

  • Byeon, SR; Park, H; Kim, H; Hong, J

Published Date

  • November 2011

Published In

Volume / Issue

  • 13 / 21

Start / End Page

  • 5816 - 5819

PubMed ID

  • 21988493

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol2024289


  • eng