Main Article Content
Abstract
Starting from N-boc-protected 3-formylindole, practical synthesis of carbazole alkaloids clausine E, mukonine, koenoline, murrayafoline A and murrayanine has been accomplished in overall seven steps. The application of dimethyl maleate to construct the suitably substituted aromatic ring and selective transformation of mukonine to murraya-foline A are the important features.
Keywords
Article Details
References
- J. Roy, A.K. Jana and D. Mal, Recent Trends in the Synthesis of Carbazoles: An Update, Tetrahedron, 68, 6099 (2012); https://doi.org/10.1016/j.tet.2012.05.007.
- A.W. Schmidt, K.R. Reddy and H.-J. Knölker, Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids, Chem. Rev., 112, 3193 (2012); https://doi.org/10.1021/cr200447s.
- H.-J. Knölker and K.R. Reddy, Isolation and Synthesis of Biologically Active Carbazole Alkaloids, Chem. Rev., 102, 4303 (2002); https://doi.org/10.1021/cr020059j.
- D.P. Chakraborty and S. Roy eds.: W. Merz, G.W. Kirby, W. Steglich and C. Tamm, Progress in the Chemistry of Organic Natural Products. Springer-Verlag: Wien, vol. 57, p. 71 (1991).
- G. Bringmann, A. Ledermann and G. François, Dimeric Murrayafoline A: A Ootential Bis-Carbazole Alkaloid: 'Biomimetic' Synthesis, Atropo-isomer Separation and Antimalarial Activity, Heterocycles, 40, 293 (1995); https://doi.org/10.3987/COM-94-S30.
- J.D. Crum and P.W. Sprague, The Synthesis of Murrayanine, Chem. Commun. (London), 417 (1966) https://doi.org/10.1039/C19660000417.
- D.P. Chakraborty and B.K. Chowdhury, Synthesis of Murrayanine, J. Org. Chem., 33, 1265 (1968); https://doi.org/10.1021/jo01267a083.
- C.J. Moody, Synthesis of Carbazole Alkaloids, Synlett, 681 (1994); https://doi.org/10.1055/s-1994-22975.
- H.-J. Knölker and M. Wolpert, Transition Metal Complexes in Organic Synthesis, Part 36. Cyclization of Tricarbonyliron Complexes by Oxygen to 4a,9a-Dihydro-9H-carbazoles: Application to the Synthesis of Mukonine, Mukonidine and Pyrido[3,2,1-jk]carbazoles, Tetrahedron Lett., 38, 533 (1997); https://doi.org/10.1016/S0040-4039(96)02364-7.
- H.-J. Knölker and M. Bauermeister, Tansition Metal-Diene Complexes in Organic Synthesis-16: Iron-Mediated Total Synthesis of 1-Oxygenated Carbazole Alkaloids, Tetrahedron, 49, 11221 (1993); https://doi.org/10.1016/S0040-4020(01)81809-3.
- G. Bringmann, F. Tasler, H. Endress, K. Peters and E.M. Peters, Synthesis of Mukonine and Seven Further 1-Oxygenated Carbazole Alkaloids, Synthesis, 1501 (1998); https://doi.org/10.1055/s-1998-2184.
- S.B. Markad and N.P. Argade, Diversity Oriented Convergent Access for Collective Total Synthesis of Bioactive Multifunctional Carbazole Alkaloids: Synthesis of Carbazomycin A, Carbazomycin B, Hyellazole, Chlorohyellazole and Clausenaline D, Org. Lett., 16, 5470 (2014); https://doi.org/10.1021/ol502721r.
- S.B. Markad and N.P. Argade, Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A and the Proposed Claulamine E, J. Org. Chem., 81, 5222 (2016); https://doi.org/10.1021/acs.joc.6b00702.
- S.B. Markad and N.P. Argade, Solid State Auto-Inversion of C-Centro-chirality: Enantioselective Total Synthesis of Furocarbazolones (-)-epi-Claulansine D and (-)-Claulansine D and Pyranocarbazolone (+)-epi-Claulansine C, J. Org. Chem., 83, 382 (2018); https://doi.org/10.1021/acs.joc.7b02773.
- G. Bringmann and S. Tasler, Synthesis of Methylene-bridged Binary Carbazole Alkaloids and a Related Tricarbazole, Tetrahedron, 57, 2337 (2001); https://doi.org/10.1016/S0040-4020(01)00104-1.
References
J. Roy, A.K. Jana and D. Mal, Recent Trends in the Synthesis of Carbazoles: An Update, Tetrahedron, 68, 6099 (2012); https://doi.org/10.1016/j.tet.2012.05.007.
A.W. Schmidt, K.R. Reddy and H.-J. Knölker, Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids, Chem. Rev., 112, 3193 (2012); https://doi.org/10.1021/cr200447s.
H.-J. Knölker and K.R. Reddy, Isolation and Synthesis of Biologically Active Carbazole Alkaloids, Chem. Rev., 102, 4303 (2002); https://doi.org/10.1021/cr020059j.
D.P. Chakraborty and S. Roy eds.: W. Merz, G.W. Kirby, W. Steglich and C. Tamm, Progress in the Chemistry of Organic Natural Products. Springer-Verlag: Wien, vol. 57, p. 71 (1991).
G. Bringmann, A. Ledermann and G. François, Dimeric Murrayafoline A: A Ootential Bis-Carbazole Alkaloid: 'Biomimetic' Synthesis, Atropo-isomer Separation and Antimalarial Activity, Heterocycles, 40, 293 (1995); https://doi.org/10.3987/COM-94-S30.
J.D. Crum and P.W. Sprague, The Synthesis of Murrayanine, Chem. Commun. (London), 417 (1966) https://doi.org/10.1039/C19660000417.
D.P. Chakraborty and B.K. Chowdhury, Synthesis of Murrayanine, J. Org. Chem., 33, 1265 (1968); https://doi.org/10.1021/jo01267a083.
C.J. Moody, Synthesis of Carbazole Alkaloids, Synlett, 681 (1994); https://doi.org/10.1055/s-1994-22975.
H.-J. Knölker and M. Wolpert, Transition Metal Complexes in Organic Synthesis, Part 36. Cyclization of Tricarbonyliron Complexes by Oxygen to 4a,9a-Dihydro-9H-carbazoles: Application to the Synthesis of Mukonine, Mukonidine and Pyrido[3,2,1-jk]carbazoles, Tetrahedron Lett., 38, 533 (1997); https://doi.org/10.1016/S0040-4039(96)02364-7.
H.-J. Knölker and M. Bauermeister, Tansition Metal-Diene Complexes in Organic Synthesis-16: Iron-Mediated Total Synthesis of 1-Oxygenated Carbazole Alkaloids, Tetrahedron, 49, 11221 (1993); https://doi.org/10.1016/S0040-4020(01)81809-3.
G. Bringmann, F. Tasler, H. Endress, K. Peters and E.M. Peters, Synthesis of Mukonine and Seven Further 1-Oxygenated Carbazole Alkaloids, Synthesis, 1501 (1998); https://doi.org/10.1055/s-1998-2184.
S.B. Markad and N.P. Argade, Diversity Oriented Convergent Access for Collective Total Synthesis of Bioactive Multifunctional Carbazole Alkaloids: Synthesis of Carbazomycin A, Carbazomycin B, Hyellazole, Chlorohyellazole and Clausenaline D, Org. Lett., 16, 5470 (2014); https://doi.org/10.1021/ol502721r.
S.B. Markad and N.P. Argade, Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A and the Proposed Claulamine E, J. Org. Chem., 81, 5222 (2016); https://doi.org/10.1021/acs.joc.6b00702.
S.B. Markad and N.P. Argade, Solid State Auto-Inversion of C-Centro-chirality: Enantioselective Total Synthesis of Furocarbazolones (-)-epi-Claulansine D and (-)-Claulansine D and Pyranocarbazolone (+)-epi-Claulansine C, J. Org. Chem., 83, 382 (2018); https://doi.org/10.1021/acs.joc.7b02773.
G. Bringmann and S. Tasler, Synthesis of Methylene-bridged Binary Carbazole Alkaloids and a Related Tricarbazole, Tetrahedron, 57, 2337 (2001); https://doi.org/10.1016/S0040-4020(01)00104-1.