TY - JOUR
T1 - Total synthesis of murrayanine involving 4,5-dimethyleneoxazolidin-2-ones and a palladium(0)-catalyzed diary insertion
AU - Bernal, Pablo
AU - Tamariz, Joaquin
PY - 2007
Y1 - 2007
N2 - A new total synthesis of the natural carbazole murrayanine (1) was developed by using the 4,5-dimethyleneoxazolidin-2-one 12 as starting material. The latter underwent a highly regioselective Diets - Alder cycloaddition with acrylaldehyde (= prop-2-enal; 13) to give adduct 14 (Scheme 3). Conversion of this adduct into diarylamine derivative 9 was carried out via hydrolysis and methylation (Scheme 4). Differing from our previous synthesis, in which such a diarylamine derivative was transformed into 1 by a PdII- stoichiometric cyclization, this new approach comprised an improved cyclization through a more efficient Pd0-catalyzed intramolecular diaryl coupling which was applied to 9, thus obtaining the natural carbazole 1 in a higher overall yield.
AB - A new total synthesis of the natural carbazole murrayanine (1) was developed by using the 4,5-dimethyleneoxazolidin-2-one 12 as starting material. The latter underwent a highly regioselective Diets - Alder cycloaddition with acrylaldehyde (= prop-2-enal; 13) to give adduct 14 (Scheme 3). Conversion of this adduct into diarylamine derivative 9 was carried out via hydrolysis and methylation (Scheme 4). Differing from our previous synthesis, in which such a diarylamine derivative was transformed into 1 by a PdII- stoichiometric cyclization, this new approach comprised an improved cyclization through a more efficient Pd0-catalyzed intramolecular diaryl coupling which was applied to 9, thus obtaining the natural carbazole 1 in a higher overall yield.
UR - http://www.scopus.com/inward/record.url?scp=34548402881&partnerID=8YFLogxK
U2 - 10.1002/hlca.200790148
DO - 10.1002/hlca.200790148
M3 - Artículo
AN - SCOPUS:34548402881
SN - 0018-019X
VL - 90
SP - 1449
EP - 1454
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 8
ER -