An unusual michael-induced skeletal rearrangement of a bicyclo[3.3.1]nonane framework of phloroglucinols to a novel bioactive bicyclo[3.3.0]octane

dc.contributor.author	Vidali, VP	en
dc.contributor.author	Mitsopoulou, KP	en
dc.contributor.author	Dakanali, M	en
dc.contributor.author	Demadis, KD	en
dc.contributor.author	Odysseos, AD	en
dc.contributor.author	Christou, YA	en
dc.contributor.author	Couladouros, EA	en
dc.date.accessioned	2014-06-06T06:52:17Z
dc.date.available	2014-06-06T06:52:17Z
dc.date.issued	2013	en
dc.identifier.issn	15237060	en
dc.identifier.uri	http://dx.doi.org/10.1021/ol4020909	en
dc.identifier.uri	http://62.217.125.90/xmlui/handle/123456789/5945
dc.subject.other	alkane	en
dc.subject.other	bicyclo compound	en
dc.subject.other	nonane	en
dc.subject.other	octane	en
dc.subject.other	phloroglucinol	en
dc.subject.other	article	en
dc.subject.other	chemical structure	en
dc.subject.other	chemistry	en
dc.subject.other	stereoisomerism	en
dc.subject.other	Alkanes	en
dc.subject.other	Bicyclo Compounds	en
dc.subject.other	Molecular Structure	en
dc.subject.other	Octanes	en
dc.subject.other	Phloroglucinol	en
dc.subject.other	Stereoisomerism	en
dc.title	An unusual michael-induced skeletal rearrangement of a bicyclo[3.3.1]nonane framework of phloroglucinols to a novel bioactive bicyclo[3.3.0]octane	en
heal.type	journalArticle	en
heal.identifier.primary	10.1021/ol4020909	en
heal.publicationDate	2013	en
heal.abstract	A novel skeletal rearrangement of bicyclo[3.3.1]nonane-2,4,9-trione (16) to an unprecedented highly functionalized bicyclo[3.3.0]octane system (17), induced by an intramolecular Michael addition, is presented. This novel framework was found to be similarly active to hyperforin (1), against PC-3 cell lines. A mechanistic study was examined in detail, proposing a number of cascade transformations. Also, reactivity of the Δ7,10-double bond was examined under several conditions to explain the above results. © 2013 American Chemical Society.	en
heal.journalName	Organic Letters	en
dc.identifier.issue	21	en
dc.identifier.volume	15	en
dc.identifier.doi	10.1021/ol4020909	en
dc.identifier.spage	5404	en
dc.identifier.epage	5407	en