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 journalArticle

8 Citations (Scopus)

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

Fingerprint

Diosgenin
Phytosterols
Growth Inhibitors
steroids
Ketones
synthesis
ketones
inhibitors
16-dehydropregnenolone

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Di Filippo, M., Fezza, F., Izzo, I., De Riccardis, F., & Sodano, G. (2000). Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii. European Journal of Organic Chemistry, (18), 3247-3252.

Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii. / Di Filippo, Marcello; Fezza, Filomena; Izzo, Irene; De Riccardis, Francesco; Sodano, Guido.

In: European Journal of Organic Chemistry, No. 18, 09.2000, p. 3247-3252.

Research output: Contribution to journalArticle

Di Filippo, M, Fezza, F, Izzo, I, De Riccardis, F & Sodano, G 2000, 'Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii', European Journal of Organic Chemistry, no. 18, pp. 3247-3252.
Di Filippo, Marcello ; Fezza, Filomena ; Izzo, Irene ; De Riccardis, Francesco ; Sodano, Guido. / Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii. In: European Journal of Organic Chemistry. 2000 ; No. 18. pp. 3247-3252.
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