RT journal article
T1 Synthesis of the western half of breviones C, D, F and G
A1 Macías Domínguez, Francisco Antonio
A1 Carrera Fernández, Ceferino Adrián
A1 Chinchilla Salcedo, Nuria
A1 R. Fronczek, Frank
A1 García Galindo, Juan Carlos
A2 Química Orgánica
K1 Brevianes
K1 abeo-Brevianes
K1 Tiffeneau–Demjanov
K1 Ring expansion
AB The enantioselective synthesis of the diterpenic moiety in the abeo-breviano skeleton is reported. Thesynthesis is carried out starting from 2-methyl-1,3-cyclohexanedione and EVK in eleven steps followinga ring-expansion strategy once the tricyclic perhydrophenantrene skeleton has been obtained. A newTiffeneau–Demjanov rearrangement under dark conditions is reported in which the insertion of the newmethylene group is directed towards the most hindered side of the carbonyl group. This result is new andopposite to those reported in the literature under light (filtered or un-filtered wavelengths) conditionswhere insertion in the less hindered side is usually preferred.
PB Elsevier
SN 0040-4020
YR 2010
FD 2010
LK http://hdl.handle.net/10498/30358
UL http://hdl.handle.net/10498/30358
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 04-nov-2026