Stereoselective Synthesis of (1R,5S)-4-[(E)-Alkylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones

Uroš Grošelj; David Bevk; Renata Jakše; Anton Meden; Simon Rečnik; Branko Stanovnik; Jurij Svete

doi:10.1055/s-2005-861862

PAPER

Stereoselective Synthesis of (1R,5S)-4-[(E)-Alkylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones

Uroš Grošelj, David Bevk, Renata Jakše, Anton Meden, Simon Rečnik, Branko Stanovnik, Jurij Svete*
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Akšerčeva 5, 1000 Ljubljana, Slovenia
Fax: +386(1)2419220; e-Mail: jurij.svete@uni-lj.si;

Abstract

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Abstract

Various (1R,5S)-4-[(E)-alkylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones were prepared, stereoselectively, via coupling of (1R,5S)-4-[(E)-(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one with Grignard reagents, potassium cyanide, and 2-methyl-1H-indole.

Key words

Grignard reactions - chiral pool - coupling - terpenoids - enaminones

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References

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Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 254265-254268. Copies of the data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html.