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Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Publication ,  Journal Article
Padwa, A; Wang, Q
Published in: The Journal of organic chemistry
September 2006

Several 2-imido substituted furans were found to undergo a rapid intramolecular [4 + 2]-cycloaddition to deliver oxabicyclo adducts in good to excellent yields. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, it was possible to prepare several highly functionalized tetrahydro-1H-indol-2(3H)-one derivatives which were then used to prepare several erythrina alkaloids. By taking advantage of the Rh(I)-catalyzed reaction, it was possible to convert tert-butyl 3-oxo-5-carbomethoxy-10-oxa-2-azatricyclo[5.2.1.0(1,5)]dec-8-ene-2-carboxylate into the ring opened boronate by reaction with phenylboronic acid. Treatment of the boronate with pinacol/acetic acid afforded the corresponding diol which was used in a successful synthesis of racemic 3-demethoxyerythratidinone. During the course of these studies, several novel rearrangement reactions were encountered while attempting to induce an acid-initiated Pictet Spengler cyclization of a key lactam intermediate. The IMDAF/Rh(I)-catalyzed ring opening cascade sequence was also applied to the total synthesis of (+/-)-erysotramidine as well as the lycorine type alkaloid (+/-)-epi-zephyranthine.

Duke Scholars

Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

September 2006

Volume

71

Issue

19

Start / End Page

7391 / 7402

Related Subject Headings

  • Rhodium
  • Organic Chemistry
  • Molecular Structure
  • Heterocyclic Compounds, 4 or More Rings
  • Furans
  • Erythrina
  • Cyclization
  • Catalysis
  • Alkaloids
  • 3405 Organic chemistry
 

Citation

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Padwa, A., & Wang, Q. (2006). Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans. The Journal of Organic Chemistry, 71(19), 7391–7402. https://doi.org/10.1021/jo061269p
Padwa, Albert, and Qiu Wang. “Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.The Journal of Organic Chemistry 71, no. 19 (September 2006): 7391–7402. https://doi.org/10.1021/jo061269p.
Padwa, Albert, and Qiu Wang. “Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.The Journal of Organic Chemistry, vol. 71, no. 19, Sept. 2006, pp. 7391–402. Epmc, doi:10.1021/jo061269p.
Journal cover image

Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

September 2006

Volume

71

Issue

19

Start / End Page

7391 / 7402

Related Subject Headings

  • Rhodium
  • Organic Chemistry
  • Molecular Structure
  • Heterocyclic Compounds, 4 or More Rings
  • Furans
  • Erythrina
  • Cyclization
  • Catalysis
  • Alkaloids
  • 3405 Organic chemistry