27: Some Natural and Unnatural Indoles (1990)


  • David St Clair Black School of Chemistry, University of New South Wales


Liversidge Research Lecture delivered before the Royal Society of New South Wales, September 5th, 1990, at the University of New South Wales. Reproduced by permission of the Royal Society of New South Wales from J. Proc. Roy. N.S.W., 1990, 123, 1-13.

"New reactions of specially-activated indoles provide methods by which structures related to natural products can be produced. Various 4,6-dimethoxy-substituted indoles exhibit a variety of reactions, predominantly at C7, but others at C2 or C3 instead of C7. The general increase in nucleophilic character of these indoles allows the discovery of reactions which have not been observed for other indoles. These reactions include electrophilic substitution, and addition to aldehydes and ketones. Tri-indolyl macrocycles, pyrrolo[a]indoles, cyclopentano[b]indoles and indolocarbazoles can be produced. Furthermore, new ring-fused indoles can be prepared by intramolecular nitrone 1,3-dipolar cycloaddition reactions between N1 and C2 or N1 and C7. In the latter case, similar structures can be achieved by aldol-type or organometallic reactions. The use of N-aroylindoles enables some known pyrrolophenanthridone alkaloids and some of their unknown analogs to be synthesized effectively."

Author Biography

David St Clair Black, School of Chemistry, University of New South Wales


By 1960, David St Clair Black had received his BSc and MSc from the University of Sydney, as well as an Associate Diploma in Music from the Sydney Conservatorium of Music. After many years at Monash University, in 1983, Black was appointed Department Head and Professor of Organic Chemistry at UNSW, a position he continues to hold in 2015. He has been a committee member of the Organic Chemistry Division of the International Union of Pure and Applied Chemistry since 1994, is currently IUPAC Secretary General, and was elected to the Australian Academy of Science in 2011.


For additional biographical information, photographic permissions, references and a list of honours, awards and publications, please see pages 2–4 of the transcript.


Black, D.St.C., Choy, A., Craig, D.C., Ivory, A.J. and Kumar, N., 1989a. Formation of 7,7'-bi-indolyls by oxidative dimerization of 4,6-dimethoxy-2,3-diphenylindole. Journal of the Chemical Society, Chemical Communications, 111-112.

Black, D.St.C., Craig, D.C. and Kumar, N., 1989b. Synthesis of a new class of indole-containing macrocycles. Journal of the Chemical Society, Chemical Communications, 425-426.

Black, D.St.C., Ivory, A.J., Keller, P.A. and Kumar, N., 1989c. A ready synthesis of 4-oxo-4H-pyrrolo[3,2,1-ij]quinolines. Synthesis, 322-323.

Black, D.St.C., Keller, P.A. and Kumar, N., 1989d. A direct synthesis of pyrrolophenanthridone alkaloids. Tetrahedron Letters, 30, 5807-5808.

Black, D.St.C. and Kumar, N., 1984. A general strategy for the synthesis of 2,2'-, 2,3'-, and 2,7-bi-indolyls. Journal of the Chemical Society, Chemical Communications, 441-442.

Black, D.St.C. and Kumar, N., 1990. Pyrroloquinolines. Organic Preparations and Procedures International, in press.

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Black, D.St.C., Kumar, N. and Wong, L.C.H., 1986b. Synthesis of 2-(7-indolyl)-benzimidazoles via 7-formylindoles. Synthesis, 474-476.

Black, D.St.C., Rothnie, N.E. and Wong, L.C.H., 1983. Metal template reactions. XX. Macrocyclic metal complexes derived from 4,6-dimethoxy-3-methylindole-2,7-dicarbaldehyde and some primary diamines with additional donor atoms. Australian Journal of Chemistry, 36, 2407-2412.

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Portrait of David St Clair Black