Total synthesis of (+)-isatisine A.
J Org Chem. 2010 Oct 15; 75(20):6830-41.JO

Abstract

The asymmetric total synthesis of (+)-isatisine A has been accomplished commencing with a Lewis acid-catalyzed cyclization of homochiral (S)-vinylcyclopropane diester and N-tosylindole-2-carboxaldehyde to construct the tetrahydrofuran ring. A palladium-catalyzed oxidative decarboxylation was utilized to obtain the dihydrofuran required for the subsequent dihydroxylation reaction to install the diol present on the tetrahydrofuran ring. The total synthesis was completed by an indole oxidation and electrophilic aromatic substitution sequence to construct isatisine A acetonide, which was then carried forward to the antipode of the natural product. The absolute configuration of the natural enantiomer (-)-isatisine A was determined to be C2(S), C9(R), C10(S), C12(R), and C13(R).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Karadeolian A

Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, Ontario, Canada N6A 5B7.

Kerr MA

No affiliation info available

MeSH

Indole AlkaloidsIsatinMolecular StructureStereoisomerism

Pub Type(s)

Journal Article

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

Language

eng

PubMed ID

20857988

Citation

Karadeolian, Avedis, and Michael A. Kerr. "Total Synthesis of (+)-isatisine A." The Journal of Organic Chemistry, vol. 75, no. 20, 2010, pp. 6830-41.

Karadeolian A, Kerr MA. Total synthesis of (+)-isatisine A. J Org Chem. 2010;75(20):6830-41.

Karadeolian, A., & Kerr, M. A. (2010). Total synthesis of (+)-isatisine A. The Journal of Organic Chemistry, 75(20), 6830-41. https://doi.org/10.1021/jo101209y

Karadeolian A, Kerr MA. Total Synthesis of (+)-isatisine A. J Org Chem. 2010 Oct 15;75(20):6830-41. PubMed PMID: 20857988.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Total synthesis of (+)-isatisine A. AU - Karadeolian,Avedis, AU - Kerr,Michael A, PY - 2010/9/23/entrez PY - 2010/9/23/pubmed PY - 2011/1/28/medline SP - 6830 EP - 41 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 20 N2 - The asymmetric total synthesis of (+)-isatisine A has been accomplished commencing with a Lewis acid-catalyzed cyclization of homochiral (S)-vinylcyclopropane diester and N-tosylindole-2-carboxaldehyde to construct the tetrahydrofuran ring. A palladium-catalyzed oxidative decarboxylation was utilized to obtain the dihydrofuran required for the subsequent dihydroxylation reaction to install the diol present on the tetrahydrofuran ring. The total synthesis was completed by an indole oxidation and electrophilic aromatic substitution sequence to construct isatisine A acetonide, which was then carried forward to the antipode of the natural product. The absolute configuration of the natural enantiomer (-)-isatisine A was determined to be C2(S), C9(R), C10(S), C12(R), and C13(R). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20857988/Total_synthesis_of__+__isatisine_A_ L2 - https://doi.org/10.1021/jo101209y DB - PRIME DP - Unbound Medicine ER -

Tags

Total synthesis of (+)-isatisine A.J Org Chem. 2010 Oct 15; 75(20):6830-41.JO