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Novel Syntheses of ( E )‐ and ( Z )‐Volkendousin, Cytotoxic Steroids from the Plant Melia volkensii
Author(s) -
Di Filippo Marcello,
Fezza Filomena,
Izzo Irene,
De Riccardis Francesco,
Sodano Guido
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:18<3247::aid-ejoc3247>3.0.co;2-u
Subject(s) - chemistry , cytotoxic t cell , stereochemistry , biochemistry , in vitro
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.