TY - JOUR
T1 - Pedrolane, a Polycyclic Diterpene Scaffold Containing a Bicyclo[2.2.1]heptane System, from Euphorbia pedroi
AU - Ferreira, Ricardo J.
AU - Spengler, Gabriella
AU - Orthaber, Andreas
AU - Dos Santos, Daniel J.V.A.
AU - Ferreira, Maria José U.
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2021/1/15
Y1 - 2021/1/15
N2 - Pedrolide (1), a diterpenoid with an unprecedented carbon skeleton, pedrolane, containing a bicycle[2.2.1]heptane system, is reported. This structural feature is hypothesized to involve an intramolecular cyclization, via Michael addition, and a ring contraction, via 1,2-alkyl shift or a Pinacol rearrangement of rings A and B, from a tigliane-type 5/7/6/3-tetracyclic ring precursor. The structure of 1 was established using spectroscopic techniques, single-crystal X-ray diffraction, and ab initio calculations. Pedrolide reversed multidrug resistance mediated by P-glycoprotein.
AB - Pedrolide (1), a diterpenoid with an unprecedented carbon skeleton, pedrolane, containing a bicycle[2.2.1]heptane system, is reported. This structural feature is hypothesized to involve an intramolecular cyclization, via Michael addition, and a ring contraction, via 1,2-alkyl shift or a Pinacol rearrangement of rings A and B, from a tigliane-type 5/7/6/3-tetracyclic ring precursor. The structure of 1 was established using spectroscopic techniques, single-crystal X-ray diffraction, and ab initio calculations. Pedrolide reversed multidrug resistance mediated by P-glycoprotein.
UR - http://www.scopus.com/inward/record.url?scp=85099101662&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.0c03647
DO - 10.1021/acs.orglett.0c03647
M3 - Article
C2 - 33373257
AN - SCOPUS:85099101662
SN - 1523-7060
VL - 23
SP - 274
EP - 278
JO - Organic Letters
JF - Organic Letters
IS - 2
ER -