Format of Original
Chemistry, a European Journal
Original Item ID
DOI: 10.1002/chem.201501274, PubMed Central: PMID: 26096989
A series of eight stereoisomeric N-(tetrahydroxy bicyclo-[5.1.0]oct-2S*-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 1H 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 μM.
El-Mansy, Mohamed F.; Flister, Matthew; Lindeman, Sergey; Kalous, Kelsey S.; Sem, Daniel S.; and Donaldson, William, "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols" (2015). Chemistry Faculty Research and Publications. 470.