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Free Radical Macrocyclizations from Steroid-Derived Precursors

Publication ,  Journal Article
Scott, DM; McPhail, AT; Porter, NA
Published in: Journal of Organic Chemistry
January 1, 1993

Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functionality. Free radical initiation in the presence of a polymerizable olefin resulted in the formation of macrocycles that had incorporated monomer. The yield of macrocycle formed was as high as 51% for templates derived from lithocholic acid whereas templates derived from androstanolone failed to give significant amounts of macrocycles. The effects of variation of initiating and terminating functionality, steroid, and olefin on macrocycle size and yield were examined. © 1993, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1993

Volume

58

Issue

5

Start / End Page

1178 / 1186

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Chicago
ICMJE
MLA
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Scott, D. M., McPhail, A. T., & Porter, N. A. (1993). Free Radical Macrocyclizations from Steroid-Derived Precursors. Journal of Organic Chemistry, 58(5), 1178–1186. https://doi.org/10.1021/jo00057a034
Scott, D. M., A. T. McPhail, and N. A. Porter. “Free Radical Macrocyclizations from Steroid-Derived Precursors.” Journal of Organic Chemistry 58, no. 5 (January 1, 1993): 1178–86. https://doi.org/10.1021/jo00057a034.
Scott DM, McPhail AT, Porter NA. Free Radical Macrocyclizations from Steroid-Derived Precursors. Journal of Organic Chemistry. 1993 Jan 1;58(5):1178–86.
Scott, D. M., et al. “Free Radical Macrocyclizations from Steroid-Derived Precursors.” Journal of Organic Chemistry, vol. 58, no. 5, Jan. 1993, pp. 1178–86. Scopus, doi:10.1021/jo00057a034.
Scott DM, McPhail AT, Porter NA. Free Radical Macrocyclizations from Steroid-Derived Precursors. Journal of Organic Chemistry. 1993 Jan 1;58(5):1178–1186.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

January 1, 1993

Volume

58

Issue

5

Start / End Page

1178 / 1186

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry