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An Improved Route to (+)‐Tedanolide and Analysis of Its Subtle Effects Controlling Conformation and Biological Behaviour
Author(s) -
Diaz Nina,
Zhu Mingzhao,
Ehrlich Gunnar,
Eggert Ulrike,
Muthukumar Yazh,
Sasse Florenz,
Kalesse Markus
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103038
Subject(s) - aldol reaction , natural product , ketone , combinatorial chemistry , chemistry , stereochemistry , biochemistry , organic chemistry , catalysis
The improved synthesis of the antitumor compound (+)‐tedanolide is described through an aldol coupling of bis‐ketone 7 . This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des‐epoxy‐tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.