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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

MPG-Autoren
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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Guth,  Oliver
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Düffels,  Arno
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Liebl,  Monika
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gabor,  Barbara
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mynott,  Richard
Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zitation

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.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-0024-4607-7
Zusammenfassung
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.