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

Publication ,  Journal Article
Wang, Q; Padwa, A
Published in: Organic letters
June 2004

[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.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

June 2004

Volume

6

Issue

13

Start / End Page

2189 / 2192

Related Subject Headings

  • Stereoisomerism
  • Rhodium
  • Phenanthridines
  • Organic Chemistry
  • Indoles
  • Furans
  • Catalysis
  • Bridged Bicyclo Compounds, Heterocyclic
  • Amaryllidaceae Alkaloids
  • Alkaloids
 

Citation

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MLA
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Wang, Q., & Padwa, A. (2004). Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine. Organic Letters, 6(13), 2189–2192. https://doi.org/10.1021/ol049348f
Wang, Qiu, and Albert Padwa. “Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.Organic Letters 6, no. 13 (June 2004): 2189–92. https://doi.org/10.1021/ol049348f.
Wang, Qiu, and Albert Padwa. “Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.Organic Letters, vol. 6, no. 13, June 2004, pp. 2189–92. Epmc, doi:10.1021/ol049348f.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

June 2004

Volume

6

Issue

13

Start / End Page

2189 / 2192

Related Subject Headings

  • Stereoisomerism
  • Rhodium
  • Phenanthridines
  • Organic Chemistry
  • Indoles
  • Furans
  • Catalysis
  • Bridged Bicyclo Compounds, Heterocyclic
  • Amaryllidaceae Alkaloids
  • Alkaloids