Ruthenium-Catalyzed Hydrovinylation of Dienoates: Model Studies Directed Toward the C10-C18 Segment of Ambruticin

Zhengjie He; Chae S. Yi; William A. Donaldson

doi:10.1055/s-2004-825605

LETTER

Ruthenium-Catalyzed Hydrovinylation of Dienoates: Model Studies Directed Toward the C10-C18 Segment of Ambruticin

Zhengjie He, Chae S. Yi*, William A. Donaldson*
Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881, USA
Fax: +1(414)2887066; e-Mail: william.donaldson@marquette.edu;

Abstract

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Abstract

The ruthenium-catalyzed hydrovinylation of 2,4-dienoates 3 proceeds in a regioselective fashion to give 4-alkyl-2,5-dienoates 4 in good yields. Olefin cross-metathesis of a vinylcyclopropane with 4e demonstrates a synthetic route to the C10-C18 segment of ambruticin.

Key words

ruthenium catalysis - hydrovinylation - cross-metathesis

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References

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14: ¹H NMR (CDCl₃): δ = 7.15-7.05 (m, 6 H), 6.94-6.91 (m, 4 H), 5.74 (dd, J = 0.9, 9.9 Hz, 1 H), 5.66 (dd, J = 6.6, 15.3 Hz, 1 H), 5.41 (dd, J = 7.6, 15.3 Hz, 1 H), 4.23 (q, J = 7.2 Hz, 2 H), 3.93 (m, 1 H), 2.51 (d, J = 5.7 Hz, 2 H), 2.31 (m, 1 H), 1.95 (s, 3 H), 1.35 (t, J = 7.2 Hz, 3 H), 1.15 (d, J = 6.6 Hz, 3 H). ¹³C NMR (CDCl₃): δ = 167.2, 145.1, 137.1, 132.4, 130.1, 128.3, 127.2, 125.2, 60.3, 36.4, 33.1, 29.4, 21.3, 21.0, 14.9. FAB-HRMS: m/z [M + Li⁺] calcd for C₂₅H₂₈O₂Li: 367.2249; found: 367.2263.