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  Indenylidene Complexes of Ruthenium: Optimized Synthesis, Structure Elucidation, and Performance as Catalysts for Olefin Metathesis—Application to the Synthesis of the ADE-Ring System of Nakadomarin A

Fürstner, A., Guth, O., Düffels, A., Seidel, G., Liebl, M., Gabor, B., et al. (2001). Indenylidene Complexes of Ruthenium: Optimized Synthesis, Structure Elucidation, and Performance as Catalysts for Olefin Metathesis—Application to the Synthesis of the ADE-Ring System of Nakadomarin A. Chemistry – A European Journal, 7(22), 4811-4820. doi:10.1002/1521-3765(20011119)7:22<4811:AID-CHEM4811>3.0.CO;2-P.

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 Creators:
Fürstner, Alois1, Author           
Guth, Oliver1, Author           
Düffels, Arno1, Author
Seidel, Günter1, Author           
Liebl, Monika1, Author           
Gabor, Barbara2, Author           
Mynott, Richard2, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              

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Free keywords: alkenes; carbenes; metathesis; natural products; ruthenium
 Abstract: An optimized and large scale adaptable synthesis of the ruthenium phenylindenylidene complex 3 is described which employs commercially available diphenyl propargyl alcohol 5 as a stable and convenient carbene source. Previous ambiguities as to the actual structure of the complex have been ruled out by a full analysis of its NMR spectra. A series of applications to ring closing metathesis (RCM) reactions shows that complex 3 is as good as or even superior to the classical Grubbs carbene 1 in terms of yield, reaction rate, and tolerance towards polar functional groups. Complex 3 turns out to be the catalyst of choice for the synthesis of the enantiopure core segment 77 of the marine alkaloid nakadomarin A 60 comprising the ADE rings of this target. Together with a series of other examples, this particular application illustrates that catalyst 3 is particularly well suited for the cyclization of medium-sized rings by RCM. Other key steps en route to nakadomarin A are a highly selective intramolecular Michael addition setting the quaternary center at the juncture of the A and D rings and a Takai–Nozaki olefination of aldehyde 73 with CH2I2, Ti(OiPr)4 and activated zinc dust.

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Language(s): eng - English
 Dates: 2001-05-152001-11-122001-11-19
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: 10 Volume / Issue: 7 (22) Sequence Number: - Start / End Page: 4811 - 4820 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058