Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors

Baran, Arif

dc.contributor.authors	Baran, A; Guenel, A; Balci, M;
dc.date.accessioned	2020-02-24T14:14:11Z
dc.date.available	2020-02-24T14:14:11Z
dc.date.issued	2008
dc.identifier.citation	Baran, A; Guenel, A; Balci, M; (2008). Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors. JOURNAL OF ORGANIC CHEMISTRY, 73, 4375-4370
dc.identifier.issn	0022-3263
dc.identifier.uri	https://doi.org/10.1021/jo800553u
dc.identifier.uri	https://hdl.handle.net/20.500.12619/44692
dc.description.abstract	For the construction of the bicyclo[2.2.2] octane skeleton, 2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole was reacted with vinylene carbonate to give two isomeric cycloadditon products having the bicyclo[2.2.2]octane skeleton. Hydrolysis of the ketal ring and the opening of the carbonate functionality, followed by hydroxylation of the remaining double bond resulted in the formation of a symmetrical hexol. Epoxidation of the double bond in the cycloaddition products and the subsequent ring-opening reactions produce two additional hexol derivatives. One of the synthesized molecules exhibited enzyme-specific inhibition against alpha-glycosidase.
dc.language	English
dc.publisher	AMER CHEMICAL SOC
dc.subject	Chemistry
dc.title	Synthesis of bicyclo[2.2.2]octane-2,3,5,6,7,8 hexols (Bishomoinositols) as glycosidase inhibitors
dc.type	Article
dc.identifier.volume	73
dc.identifier.startpage	4370
dc.identifier.endpage	4375
dc.contributor.department	Sakarya Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü
dc.contributor.saüauthor	Baran, Arif
dc.relation.journal	JOURNAL OF ORGANIC CHEMISTRY
dc.identifier.wos	WOS:000256757100003
dc.identifier.doi	10.1021/jo800553u
dc.contributor.author	Baran, Arif