TY - JOUR
T1 - Total Synthesis of the Natural Carbazoles O -Demethylmurrayanine and Murrastanine A, and of a C4,C4′ Symmetric Murrastanine A Dimer from N -Phenyl-4,5-dimethylene-1,3-oxazolidin-2-one
AU - Avila-Melo, José Luis
AU - Benavides, Adriana
AU - Fuentes-Gutiérrez, Alfredo
AU - Tamariz, Joaquín
AU - Jiménez-Vázquez, Hugo A.
N1 - Publisher Copyright:
© 2021 Georg Thieme Verlag. All rights reserved.
PY - 2021/3/1
Y1 - 2021/3/1
N2 - The synthesis of natural carbazoles O -demethylmurrayanine and murrastanine A starting from the title exo -heterocyclic diene- is described. In the synthesis of murrastanine A, its symmetric C4,C4′ dimer can be obtained as the sole product under rather mild conditions. In all cases, the key intermediate is the same diarylamine. The carbazole nucleus is obtained through a Pd-promoted cyclization of the appropriate diarylamine. For the synthesis of O -demethylmurrayanine, the cyclization takes place on a silylated derivative. The crystal structures of murrayanine, two diarylamines, and two non-natural carbazole intermediates are also presented.
AB - The synthesis of natural carbazoles O -demethylmurrayanine and murrastanine A starting from the title exo -heterocyclic diene- is described. In the synthesis of murrastanine A, its symmetric C4,C4′ dimer can be obtained as the sole product under rather mild conditions. In all cases, the key intermediate is the same diarylamine. The carbazole nucleus is obtained through a Pd-promoted cyclization of the appropriate diarylamine. For the synthesis of O -demethylmurrayanine, the cyclization takes place on a silylated derivative. The crystal structures of murrayanine, two diarylamines, and two non-natural carbazole intermediates are also presented.
KW - Diels-Alder cycloaddition
KW - O-demethylmurrayanine
KW - Pd(II)-promoted diarylamine coupling
KW - biscarbazoles
KW - exo -heterocyclic dienes
KW - murrastanine A
KW - natural carbazole synthesis
UR - http://www.scopus.com/inward/record.url?scp=85102152688&partnerID=8YFLogxK
U2 - 10.1055/a-1385-9052
DO - 10.1055/a-1385-9052
M3 - Artículo
AN - SCOPUS:85102152688
SN - 0039-7881
VL - 53
SP - 2201
EP - 2211
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 13
ER -