A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

TY - JOUR

T1 - A strategic approach to [6,6]-bicyclic lactones

T2 - application towards the CD fragment of DHβE

AU - Jepsen, Tue Heesgaard

AU - Glibstrup, Emil

AU - Crestey, Francois Louis Jean

AU - Jensen, Anders A.

AU - Kristensen, Jesper Langgaard

PY - 2017/5/22

Y1 - 2017/5/22

N2 - We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

AB - We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

U2 - 10.3762/bjoc.13.98

DO - 10.3762/bjoc.13.98

M3 - Journal article

C2 - 28684978

SN - 2195-951X

VL - 13

SP - 988

EP - 994

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -