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Total synthesis of (-)-isatisine A.
J Org Chem. 2012 Dec 07; 77(23):10509-15.JO

Abstract

A modular total synthesis of (-)-isatisine A is described in which four consecutive metal-mediated transformations have been employed at the final stage. These include [Pd]-catalyzed Sonogashira coupling, [Pd]-catalyzed nitroalkyne cycloisomerization leading to isatogens, and addition of indoles to isatogens using InCl(3)- and [Rh]-catalyzed oxidative N-heterocyclization of amino alcohol to form the key amide bond. In addition to these, the removal of the protecting groups has also been carried out in a selective fashion employing either catalytic or stoichiometric metal/metal-based reagents.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Patel P
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhaba Road, Pune-411008, India.
Ramana CV
No affiliation info available

MeSH

AmidesAmino AlcoholsCatalysisIndicators and ReagentsIndole AlkaloidsIsatinMolecular StructureOxidation-ReductionPalladium

Pub Type(s)

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

Language

eng

PubMed ID

23153399

Citation

Patel, Pitambar, and C V. Ramana. "Total Synthesis of (-)-isatisine A." The Journal of Organic Chemistry, vol. 77, no. 23, 2012, pp. 10509-15.
Patel P, Ramana CV. Total synthesis of (-)-isatisine A. J Org Chem. 2012;77(23):10509-15.
Patel, P., & Ramana, C. V. (2012). Total synthesis of (-)-isatisine A. The Journal of Organic Chemistry, 77(23), 10509-15. https://doi.org/10.1021/jo302198v
Patel P, Ramana CV. Total Synthesis of (-)-isatisine A. J Org Chem. 2012 Dec 7;77(23):10509-15. PubMed PMID: 23153399.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (-)-isatisine A. AU - Patel,Pitambar, AU - Ramana,C V, Y1 - 2012/11/20/ PY - 2012/11/17/entrez PY - 2012/11/17/pubmed PY - 2013/6/19/medline SP - 10509 EP - 15 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 23 N2 - A modular total synthesis of (-)-isatisine A is described in which four consecutive metal-mediated transformations have been employed at the final stage. These include [Pd]-catalyzed Sonogashira coupling, [Pd]-catalyzed nitroalkyne cycloisomerization leading to isatogens, and addition of indoles to isatogens using InCl(3)- and [Rh]-catalyzed oxidative N-heterocyclization of amino alcohol to form the key amide bond. In addition to these, the removal of the protecting groups has also been carried out in a selective fashion employing either catalytic or stoichiometric metal/metal-based reagents. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23153399/Total_synthesis_of_____isatisine_A_ L2 - https://doi.org/10.1021/jo302198v DB - PRIME DP - Unbound Medicine ER -