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Derivatives of (–)‐Isosteviol with Expanded Ring D and Various Oxygen Functionalities
Author(s) -
Lohoelter Christina,
Schollmeyer Dieter,
Waldvogel Siegfried R.
Publication year - 2012
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/ejoc.201200970
Subject(s) - chemistry , moiety , ring (chemistry) , supramolecular chemistry , stereochemistry , block (permutation group theory) , combinatorial chemistry , oxygen , molecule , organic chemistry , combinatorics , mathematics
(–)‐Isosteviol is a unique ex‐chiral‐pool building block that is readily available. Both functional groups are aligned in a concave manner. The methyl moiety on the backbone also points in this direction, creating a strong asymmetric environment close to these functional groups. The slightly divergent orientation of the keto and carboxy functions limits its use in the construction of supramolecular architectures as optically pure divalent building blocks. By selective transformations, ring D of (–)‐isosteviol can be expanded and equipped with oxygen‐containing functionalities, providing a variety of useful and rigid building blocks with defined stereochemistry.