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Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II

Publication ,  Journal Article
Adler, MJ; Baldwin, SW
Published in: Tetrahedron Letters
September 9, 2009

Herein is reported an efficient method for the synthesis of 2,2-dimethyl-2H-chromenes in a single step from the corresponding phenol and 3-methyl-2-butenal via microwave irradiation in CDCl3. This protocol features a mild reaction environment (neutral, no added catalyst) which yields regioselective formation of the chromene and displays tolerance toward acid- and base-sensitive protecting groups. © 2009 Elsevier Ltd. All rights reserved.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

September 9, 2009

Volume

50

Issue

36

Start / End Page

5075 / 5079

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Adler, M. J., & Baldwin, S. W. (2009). Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II. Tetrahedron Letters, 50(36), 5075–5079. https://doi.org/10.1016/j.tetlet.2009.06.090
Adler, M. J., and S. W. Baldwin. “Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II.” Tetrahedron Letters 50, no. 36 (September 9, 2009): 5075–79. https://doi.org/10.1016/j.tetlet.2009.06.090.
Adler, M. J., and S. W. Baldwin. “Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II.” Tetrahedron Letters, vol. 50, no. 36, Sept. 2009, pp. 5075–79. Scopus, doi:10.1016/j.tetlet.2009.06.090.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

September 9, 2009

Volume

50

Issue

36

Start / End Page

5075 / 5079

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry