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Mild Thio‐Diversification of Bioactive Natural Products. Withaferin A: A Case study.
Author(s) -
Casero C. N.,
Novillo J. N. Garay,
García M. E.,
Oberti J. C.,
Nicotra V. E.,
Peñéñory A. B.,
Bisogno F. R.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701870
Subject(s) - thio , chemistry , stereocenter , sulfur , diversification (marketing strategy) , ring (chemistry) , natural product , nucleophile , combinatorial chemistry , organic chemistry , business , catalysis , marketing , enantioselective synthesis
A sustainable strategy was developed to create chemical diversity from bioactive scaffolds. The methodology comprises a set of simple reactions between the parent compound (i. e. withaferin A), and small sulfur nucleophiles in hydroalcoholic media, at room temperature and in open‐air atmosphere. Novel steroidal sulfur natural product‐analogs were obtained, featuring ring opening, ring formation, new stereocenters and modulation of parameters useful in medicinal chemistry.