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Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols
Author(s) -
ElMansy Mohamed F.,
Flister Matthew,
Lindeman Sergey,
Kalous Kelsey,
Sem Daniel S.,
Donaldson William A.
Publication year - 2015
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.201501274
Subject(s) - cyclooctatetraene , chemistry , organic chemistry , molecule
A series of eight stereoisomeric N ‐(tetrahydroxy bicyclo‐[5.1.0]oct‐2 S *‐yl)phthalimides were prepared in one to four steps from N ‐(bicyclo[5.1.0]octa‐3,5‐dien‐2‐yl)phthalimide (±)‐ 7 , which is readily available from cyclooctatetraene (62 % yield). The structural assignments of the stereoisomers were established by 1 H NMR spectral data as well as X‐ray crystal structures for certain members. The outcomes of several epoxydiol hydrolyses, particularly ring contraction and enlargement, are of note. The isomeric phthalimides as well as the free amines did not exhibit β‐glucosidase inhibitory activity at a concentration of less than 100 μ M .