Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole

The synthesis of seven pyrano[3,2-a]carbazole alkaloids has been achieved using their putative biogenetic precursor 2-hydroxy-6-methylcarbazole as key intermediate.

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Divergent Total Synthesis of (±)‐Mahanine and Other Carbazole Alkaloids

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.202100176 ◽

2021 ◽

Author(s):

Ranjan Jana ◽

Arghya Polley ◽

Kasarla Varalaxmi ◽

Arijit Nandi

Keyword(s):

Total Synthesis ◽

Carbazole Alkaloids

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Transition Metal Complexes in Organic Synthesis. Part 81. First Total Synthesis of the 7-Oxygenated Carbazole Alkaloids Clauszoline-K (IIIa), 3-Formyl-7-hydroxycarbazole (IIIb), Clausine M (IIIc), Clausine N (IIId) and the anti-HIV Active Siamenol (IV) Using a Highly Efficient Palladium-Catalyzed Approach.

ChemInform ◽

10.1002/chin.200702192 ◽

2007 ◽

Vol 38 (2) ◽

Author(s):

Micha P. Krahl ◽

Anne Jaeger ◽

Tilo Krause ◽

Hans-Joachim Knoelke

Keyword(s):

Transition Metal ◽

Total Synthesis ◽

Metal Complexes ◽

Organic Synthesis ◽

Transition Metal Complexes ◽

Highly Efficient ◽

Palladium Catalyzed ◽

Anti Hiv ◽

Carbazole Alkaloids

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ChemInform Abstract: STEREOSELECTIVE TOTAL SYNTHESIS OF (.+-.)-TRICHODIENE: BIOGENETIC PRECURSOR OF THE TRICHOTHECANE SESQUITERPENOIDS

Chemischer Informationsdienst ◽

10.1002/chin.198106300 ◽

1981 ◽

Vol 12 (6) ◽

Author(s):

S. C. WELCH ◽

A. S. C. PRAKASA RAO ◽

C. G. GIBBS ◽

R. Y. WONG

Keyword(s):

Total Synthesis ◽

Biogenetic Precursor

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Total synthesis of carbazole alkaloids

Tetrahedron ◽

10.1016/j.tet.2019.01.003 ◽

2019 ◽

Vol 75 (7) ◽

pp. 874-887 ◽

Cited By ~ 1

Author(s):

Bharath kumar goud Bhatthula ◽

Janardhan reddy Kanchani ◽

Veera reddy Arava ◽

M.C.S. Subha

Keyword(s):

Total Synthesis ◽

Carbazole Alkaloids

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ChemInform Abstract: Transition Metal Complexes in Organic Synthesis. Part 109. Efficient Construction of Pyrano[3,2-a]carbazoles: Application to a Biomimetic Total Synthesis of Cyclized Monoterpenoid Pyrano[3,2-a]carbazole Alkaloids.

ChemInform ◽

10.1002/chin.201413216 ◽

2014 ◽

Vol 45 (13) ◽

pp. no-no

Author(s):

Ronny Hesse ◽

Konstanze K. Gruner ◽

Olga Kataeva ◽

Arndt W. Schmidt ◽

Hans-Joachim Knoelker

Keyword(s):

Transition Metal ◽

Total Synthesis ◽

Metal Complexes ◽

Organic Synthesis ◽

Transition Metal Complexes ◽

Efficient Construction ◽

Carbazole Alkaloids

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ChemInform Abstract: TOTAL SYNTHESIS OF THE MACROCYCLIC DITERPENE (-)-CASBENE, THE PUTATIVE BIOGENETIC PRECURSOR OF LATHYRANE, TIGLIANE, INGENANE, AND RELATED TERPENOID STRUCTURES

Chemischer Informationsdienst ◽

10.1002/chin.198046316 ◽

1980 ◽

Vol 11 (46) ◽

Author(s):

L. CROMBIE ◽

G. KNEEN ◽

G. PATTENDEN ◽

D. WHYBROW

Keyword(s):

Total Synthesis ◽

Biogenetic Precursor

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Total synthesis of the macrocyclic diterpene (–)-casbene, the putative biogenetic precursor of lathyrane, tigliane, ingenane, and related terpenoid structures

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19800001711 ◽

1980 ◽

pp. 1711-1717 ◽

Cited By ~ 28

Author(s):

Leslie Crombie ◽

Geoffrey Kneen ◽

Gerald Pattenden ◽

Derek Whybrow

Keyword(s):

Total Synthesis ◽

Biogenetic Precursor

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ChemInform Abstract: Transition Metal-Diene Complexes in Organic Synthesis. Part 16. Iron- Mediated Total Synthesis of 1-Oxygenated Carbazole Alkaloids.

ChemInform ◽

10.1002/chin.199411264 ◽

2010 ◽

Vol 25 (11) ◽

pp. no-no

Author(s):

H.-J. KNOELKER ◽

M. BAUERMEISTER

Keyword(s):

Transition Metal ◽

Total Synthesis ◽

Organic Synthesis ◽

Carbazole Alkaloids

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Transition Metals in Organic Synthesis, Part 85. A General Approach to 1,6-Dioxygenated Carbazole Alkaloids - First Total Synthesis of Clausine G, Clausine I, and Clausine Z

Synlett ◽

10.1055/s-2008-1077855 ◽

2008 ◽

Vol 2008 (11) ◽

pp. 1698-1702 ◽

Cited By ~ 5

Author(s):

Hans-Joachim Knölker ◽

Carsten Börger

Keyword(s):

Transition Metals ◽

Total Synthesis ◽

Organic Synthesis ◽

Carbazole Alkaloids

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Palladium(ii)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids

Organic & Biomolecular Chemistry ◽

10.1039/c4ob00367e ◽

2014 ◽

Vol 12 (23) ◽

pp. 3866-3876 ◽

Cited By ~ 54

Author(s):

Ronny Hesse ◽

Anne Jäger ◽

Arndt W. Schmidt ◽

Hans-Joachim Knölker

Keyword(s):

Total Synthesis ◽

Naturally Occurring ◽

Carbazole Alkaloids

Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A–E,O-methylmurrayamine A andO-methylmahanine) have been synthesised using a palladium(ii)-catalysed cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.

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