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(–)‐Isosteviol as a Versatile Ex‐Chiral‐Pool Building Block for Organic Chemistry
Author(s) -
Lohoelter Christina,
Weckbecker Magdalena,
Waldvogel Siegfried R.
Publication year - 2013
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.201300447
Subject(s) - chemistry , supramolecular chemistry , organocatalysis , block (permutation group theory) , scaffold , enantioselective synthesis , green chemistry , organic chemistry , group (periodic table) , combinatorial chemistry , nanotechnology , catalysis , molecule , computer science , mathematics , database , geometry , materials science
(–)‐Isosteviol is readily available in large quantities by the acidic treatment of a common alternative sweetener. The two functional groups of (–)‐isosteviol are presented on the same side of the ent ‐beyerane scaffold with a mutual C–C distance of about 7 Å. Their unique concave arrangement experiences a strong asymmetric environment due to an adjacent methyl group. Consequently, this building block has found several applications in supramolecular chemistry and organocatalysis. These areas and the chemical modification of this scaffold as well as its biological activity are surveyed.