TY - JOUR
T1 - Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones
AU - Bautista, Rafael
AU - Montoya, Pablo A.
AU - Rebollar, Araceli
AU - Burgueño, Eleuterio
AU - Tamariz, Joaquín
PY - 2013/9
Y1 - 2013/9
N2 - A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.
AB - A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.
KW - 2-oxygenated carbazoles
KW - Clausine V
KW - Enaminones
KW - Glycoborine
KW - Palladium(II) cyclization
UR - http://www.scopus.com/inward/record.url?scp=84885171262&partnerID=8YFLogxK
U2 - 10.3390/molecules180910334
DO - 10.3390/molecules180910334
M3 - Artículo
SN - 1420-3049
VL - 18
SP - 10334
EP - 10351
JO - Molecules
JF - Molecules
IS - 9
ER -