TY - JOUR
T1 - 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
AU - Vidali, Veroniki P.
AU - Mitsopoulou, Kornilia P.
AU - Dakanali, Marianna
AU - Demadis, Konstantinos D.
AU - Odysseos, Andreani D.
AU - Christou, Yiota A.
AU - Couladouros, Elias A.
PY - 2013/11/1
Y1 - 2013/11/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84887109352&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84887109352&partnerID=8YFLogxK
U2 - 10.1021/ol4020909
DO - 10.1021/ol4020909
M3 - Article
C2 - 24117171
AN - SCOPUS:84887109352
SN - 1523-7060
VL - 15
SP - 5404
EP - 5407
JO - Organic Letters
JF - Organic Letters
IS - 21
ER -