Synthesis, Table of Contents Synthesis 2021; 53(13): 2201-2211DOI: 10.1055/a-1385-9052 paper 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 José Luis Avila-Melo , Adriana Benavides∗ , Alfredo Fuentes-Gutiérrez , Joaquín Tamariz , Hugo A. Jiménez-Vázquez ∗ Recommend Article Abstract Buy Article All articles of this category Abstract 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. Key words Key words O-demethylmurrayanine - murrastanine A - natural carbazole synthesis - biscarbazoles - Pd(II)-promoted diarylamine coupling - exo-heterocyclic dienes - Diels–Alder cycloaddition Full Text References References 1 Chakraborty DP, Barman BK, Bose PK. Tetrahedron 1965; 21: 681 2 Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193 3 Knölker H.-J, Reddy KR. In The Alkaloids: Chemistry and Biology, Vol. 65. Cordell GA. Academic Press; New York: 2008: 1-430 4 Ngadjui BT, Ayafor JF, Sondengam BL, Connolly JD. Phytochemistry 1989; 28: 1517 5 Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H. J. Nat. Prod. 2000; 63: 125 6 Sripisut T, Laphookhieo S. J. Asian Nat. Prod. Res. 2010; 12: 614 7 Peng W.-W, Liu X.-Y, Zeng G.-Z, Tan N.-H. Chin. Tradit. 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