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 language | English |
|---|---|
| Pages (from-to) | 3247-3252 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 18 |
| Publication status | Published - Sep 2000 |
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Keywords
- Melia volkensii
- Natural products
- Steroids
- Toxicology
- Volkendousin
ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
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TY - JOUR
T1 - Novel syntheses of (E)- and (Z)-volkendousin, cytotoxic steroids from the plant Melia volkensii
AU - Di Filippo, Marcello
AU - Fezza, Filomena
AU - Izzo, Irene
AU - De Riccardis, Francesco
AU - Sodano, Guido
PY - 2000/9
Y1 - 2000/9
N2 - 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.
AB - 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.
KW - Melia volkensii
KW - Natural products
KW - Steroids
KW - Toxicology
KW - Volkendousin
UR - http://www.scopus.com/inward/record.url?scp=0033799323&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033799323&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0033799323
SP - 3247
EP - 3252
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 18
ER -