Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii

Marcello Di Filippo, Filomena Fezza, Irene Izzo, Francesco De Riccardis, Guido Sodano

Research output: Contribution to journalArticlepeer-review

Abstract

New syntheses of naturally occurring cytotoxic plant steroids (E)- and (Z)-volkendousin (1 and 2) and their acetonides 1a - a potent selective cell growth inhibitor - and 2a have been accomplished, starting from diosgenin (overall yields of 1.2%, 0.7%, 1.9%, and 1.1% for 1, 2, 1a, and 2a, respectively), and also from 16-dehydropregnenolone (overall yields of 9.4%, 2.5%, 14.0%, and 3.8% for 1, 2, 1a, and 2a, respectively). The efficiency of the stereospecific Petrow rearrangement and the straightforward introduction of the α,β-unsaturated ketone functionality, by a Wharton reaction, illustrate the utility of this new synthetic strategy.

Original languageEnglish
Pages (from-to)3247-3252
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number18
Publication statusPublished - Sep 2000

Keywords

  • Melia volkensii
  • Natural products
  • Steroids
  • Toxicology
  • Volkendousin

ASJC Scopus subject areas

  • Organic Chemistry

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