TY - JOUR
T1 - Towards the total synthesis of Pl-3
T2 - Preparation of the eastern fragment through a diastereoselective SmI2-mediated reformatsky reaction
AU - Fürst, Rita
AU - Lentsch, Christoph
AU - Rinner, Uwe
PY - 2013/4
Y1 - 2013/4
N2 - The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available D-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.
AB - The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available D-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI2-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes.
KW - Diastereoselectivity
KW - Multidrug resistance
KW - Natural products
KW - Samarium
KW - Terpenoids
UR - http://www.scopus.com/inward/record.url?scp=84876185640&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84876185640&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201300148
DO - 10.1002/ejoc.201300148
M3 - Article
AN - SCOPUS:84876185640
SN - 1434-193X
SP - 2293
EP - 2297
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 12
ER -