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• W2090161421 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." @default.
• W2090161421 created "2016-06-24" @default.
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• W2090161421 creator A5087961708 @default.
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• W2090161421 date "2001-11-19" @default.
• W2090161421 modified "2023-10-14" @default.
• W2090161421 title "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" @default.
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• W2090161421 doi "https://doi.org/10.1002/1521-3765(20011119)7:22<4811::aid-chem4811>3.0.co;2-p" @default.
• W2090161421 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11763450" @default.
• W2090161421 hasPublicationYear "2001" @default.
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