Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

Journal Article (Journal Article)

[reaction: see text] A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, the cis-diol stereochemistry of epi-zephyranthine was established.

Full Text

Duke Authors

Cited Authors

  • Wang, Q; Padwa, A

Published Date

  • June 2004

Published In

Volume / Issue

  • 6 / 13

Start / End Page

  • 2189 - 2192

PubMed ID

  • 15200317

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol049348f


  • eng