Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E
Publication type: Journal Article
Publication date: 2016-06-07
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27227838
Organic Chemistry
Abstract
The common precursor 1-methoxy-2-prenyl-3-carbomethoxycarbazole was synthesized from dimethyl indolylmethylenesuccinate in four steps. Well-planned reductive and/or oxidative transformations and intramolecular cyclizations were performed on a pivotal common precursor to accomplish collective first total synthesis of titled natural products and proposed claulamine E. Burgess reagent induced formation of kinetically controlled product claulamine A, and intramolecular cyclizations to form bicyclic claulansine A were the key reactions. An alternatively attempted synthesis failed to provide the structural isomer of proposed claulamine E.
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Total citations:
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Citations from 2024:
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(19.05%)
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Markad S. B., Argade N. P. Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E // Journal of Organic Chemistry. 2016. Vol. 81. No. 12. pp. 5222-5227.
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Markad S. B., Argade N. P. Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E // Journal of Organic Chemistry. 2016. Vol. 81. No. 12. pp. 5222-5227.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.6b00702
UR - https://doi.org/10.1021/acs.joc.6b00702
TI - Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E
T2 - Journal of Organic Chemistry
AU - Markad, Shivaji B
AU - Argade, Narshinha P.
PY - 2016
DA - 2016/06/07
PB - American Chemical Society (ACS)
SP - 5222-5227
IS - 12
VL - 81
PMID - 27227838
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2016_Markad,
author = {Shivaji B Markad and Narshinha P. Argade},
title = {Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.6b00702},
number = {12},
pages = {5222--5227},
doi = {10.1021/acs.joc.6b00702}
}
Cite this
MLA
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Markad, Shivaji B., and Narshinha P. Argade. “Biomimetic Collective Total Synthesis of Bioactive Carbazole Alkaloids Indizoline, Mafaicheenamine A, Claulamine A, Claulansine A, and the Proposed Claulamine E.” Journal of Organic Chemistry, vol. 81, no. 12, Jun. 2016, pp. 5222-5227. https://doi.org/10.1021/acs.joc.6b00702.