Document Type
Article
Language
eng
Format of Original
10 p.
Publication Date
7-20-2015
Publisher
Wiley-VCH Verlag
Source Publication
Chemistry, a European Journal
Source ISSN
0947-6539
Original Item ID
DOI: 10.1002/chem.201501274, PubMed Central: PMID: 26096989
Abstract
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.
Recommended Citation
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.
https://epublications.marquette.edu/chem_fac/470
Comments
Accepted version. Chemistry, a European Journal, Vol 21, No. 30 (July 20, 2015): 10886-10895. DOI. © 2015 John Wiley & Sons, Inc. Used with permission.
This is the pre-peer reviewed version of the following article: "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols," Chemistry, a European Journal, Vol 21, No. 30 (July 20, 2015): 10886-10895. DOI.
Dr, Daniel S. Sem was affiliated with the School of Pharmacy, Concordia University Wisconsin, Mequon, WI at the time of publication.