CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS

J STOELWINDER, WJ VANZOEST, A.M. van Leusen

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Abstract

A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

Original languageEnglish
Pages (from-to)2249-2252
Number of pages4
JournalJournal of Organic Chemistry
Volume57
Issue number8
Publication statusPublished - 10-Apr-1992

Keywords

  • PHOSPHORUS ANALOGS
  • CARBONYL-COMPOUNDS
  • AMINO-ACIDS
  • DERIVATIVES
  • ISOCYANIDES
  • PEPTIDES
  • CHAIN

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