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

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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.
Author/Creator	Vidali, Veroniki P.; Mitsopoulou, Kornilia P.; Dakanali, Marianna; Demadis, Konstantinos D.; Odysseos, Andreani D.; Christou, Yiota A.; Couladouros, Elias A.
Licencee	Γεωπονικό Πανεπιστήμιο Αθηνών
Contractor	Γεωπονικό Πανεπιστήμιο Αθηνών
Contractor	Ειδικός Λογαριασμός Κονδυλίων Έρευνας Γεωπονικού Πανεπιστημίου Αθηνών
Publisher	American Chemical Society
Source	Org. Lett., 15 (21), pp 5404–5407
Language	English
Date	2013
Extent	4 pages
Identifier	DOI: 10.1021/ol4020909
Alternative Web page	http://pubs.acs.org/doi/abs/10.1021/ol4020909
Subject	χημεία βιοχημεία χημική ένωση
Keywords	Bicyclo [3.3.1] nonane, Bioactive Bicyclo [3.3.0] octane, Skeletal rearrangement, Mechanistic study, Bicyclo
Type	Text (Journal article)
Project Notes	Πράξη: Ηράκλειτος ΙΙ Μελέτη: Απομόνωση και χαρακτηρισμός συστατικών του Hypericum perforatum: Σχεδιασμός και σύνθεση αναλόγων τους με εφαρμογές στη γεωργία