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Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation.
J Org Chem. 2015 Mar 20; 80(6):2959-71.JO

Abstract

Complete details of an asymmetric synthesis of (+)-isatisine A (1) are described. The synthesis highlights the use of a highly diastereoselective Mukaiyama-type [3 + 2]-annulation of allylsilane 5 with the unsaturated aldehyde 9a to assemble the functionalized tetrahydrofuran core of isatisine A. A convergent route to the framework of the natural product was established that employed a substrate-controlled indole coupling that was followed by a late-stage intramolecular copper(I)-mediated amidation to complete the assembly of the tetracyclic framework of (+)-isatisine A. In addition, the scope of the [3 + 2]-annulation was evaluated and enhanced utilizing diastereomeric allylsilanes anti-5 and syn-5 to establish an efficient route to stereochemically well-defined tetrahydrofurans.

Authors+Show Affiliations

Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25739011

Citation

Lee, Jihoon, and James S. Panek. "Total Synthesis of (+)-isatisine A: Application of a Silicon-directed Mukaiyama-type [3 + 2]-annulation." The Journal of Organic Chemistry, vol. 80, no. 6, 2015, pp. 2959-71.
Lee J, Panek JS. Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation. J Org Chem. 2015;80(6):2959-71.
Lee, J., & Panek, J. S. (2015). Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation. The Journal of Organic Chemistry, 80(6), 2959-71. https://doi.org/10.1021/acs.joc.5b00051
Lee J, Panek JS. Total Synthesis of (+)-isatisine A: Application of a Silicon-directed Mukaiyama-type [3 + 2]-annulation. J Org Chem. 2015 Mar 20;80(6):2959-71. PubMed PMID: 25739011.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation. AU - Lee,Jihoon, AU - Panek,James S, Y1 - 2015/03/10/ PY - 2015/3/5/entrez PY - 2015/3/5/pubmed PY - 2015/12/15/medline SP - 2959 EP - 71 JF - The Journal of organic chemistry JO - J Org Chem VL - 80 IS - 6 N2 - Complete details of an asymmetric synthesis of (+)-isatisine A (1) are described. The synthesis highlights the use of a highly diastereoselective Mukaiyama-type [3 + 2]-annulation of allylsilane 5 with the unsaturated aldehyde 9a to assemble the functionalized tetrahydrofuran core of isatisine A. A convergent route to the framework of the natural product was established that employed a substrate-controlled indole coupling that was followed by a late-stage intramolecular copper(I)-mediated amidation to complete the assembly of the tetracyclic framework of (+)-isatisine A. In addition, the scope of the [3 + 2]-annulation was evaluated and enhanced utilizing diastereomeric allylsilanes anti-5 and syn-5 to establish an efficient route to stereochemically well-defined tetrahydrofurans. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/25739011/Total_synthesis_of__+__isatisine_a:_application_of_a_silicon_directed_mukaiyama_type_[3_+_2]_annulation_ L2 - https://doi.org/10.1021/acs.joc.5b00051 DB - PRIME DP - Unbound Medicine ER -
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