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  Formal Total Synthesis of (−)-Balanol:  Concise Approach to the Hexahydroazepine Segment Based on RCM

Fürstner, A., & Thiel, O. R. (2000). Formal Total Synthesis of (−)-Balanol:  Concise Approach to the Hexahydroazepine Segment Based on RCM. The Journal of Organic Chemistry, 65(6), 1738-1742. doi:10.1021/jo991611g.

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[110]SI.pdf (Supplementary material), 718KB
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Fürstner, Alois1, Author              
Thiel, Oliver R.1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: A concise synthesis of the hexahydroazepine moiety 13 of (−)-balanol 1 is described that comprises only eight steps and is distinctly shorter than all previous reported approaches to this particular compound. Sharpless epoxidation of divinylcarbinol 4 and ring closing alkene metathesis (RCM) reaction for the formation of the heterocyclic scaffold 9 constitute the key transformations of this sequence. The latter reaction is best achieved with catalytic amounts of the ruthenium indenylidene complex 18 recently reported. Furthermore, it is demonstrated that RCM can be successfully carried out even in the presence of an azido function provided that Schrock's molybdenum alkylidene complex Mo(=NAr)(=CHCMe2Ph)[OC(Me)(CF3)2]2 (Ar = 2,6-diisopropylphenyl) is used as precatalyst.

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Language(s): eng - English
 Dates: 1999-10-152000-02-232000-03-24
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jo991611g
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: 5 Volume / Issue: 65 (6) Sequence Number: - Start / End Page: 1738 - 1742 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1