Free Radical Macrocyclizations from Steroid-Derived Precursors

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Scott, DM; McPhail, AT; Porter, NA

Published Date

  • January 1, 1993

Published In

Volume / Issue

  • 58 / 5

Start / End Page

  • 1178 - 1186

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00057a034

Citation Source

  • Scopus