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InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A.
Chemistry. 2012 Jul 27; 18(31):9601-11.C

Abstract

A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon-carbon and carbon-heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl(3) as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone.

Authors+Show Affiliations

Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22763920

Citation

Kumar, Chepuri V Suneel, et al. "InCl3-mediated Addition of Indole to Isatogens: an Expeditious Synthesis of 13-deoxy-isatisine A." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 18, no. 31, 2012, pp. 9601-11.
Kumar CV, Puranik VG, Ramana CV. InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A. Chemistry. 2012;18(31):9601-11.
Kumar, C. V., Puranik, V. G., & Ramana, C. V. (2012). InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(31), 9601-11. https://doi.org/10.1002/chem.201103604
Kumar CV, Puranik VG, Ramana CV. InCl3-mediated Addition of Indole to Isatogens: an Expeditious Synthesis of 13-deoxy-isatisine A. Chemistry. 2012 Jul 27;18(31):9601-11. PubMed PMID: 22763920.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A. AU - Kumar,Chepuri V Suneel, AU - Puranik,Vedavati G, AU - Ramana,Chepuri V, Y1 - 2012/07/04/ PY - 2011/11/16/received PY - 2012/04/24/revised PY - 2012/7/6/entrez PY - 2012/7/6/pubmed PY - 2012/10/31/medline SP - 9601 EP - 11 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 31 N2 - A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon-carbon and carbon-heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl(3) as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22763920/InCl3_mediated_addition_of_indole_to_isatogens:_an_expeditious_synthesis_of_13_deoxy_isatisine_A_ L2 - https://doi.org/10.1002/chem.201103604 DB - PRIME DP - Unbound Medicine ER -