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. Author manuscript; available in PMC: 2011 Feb 1.
Published in final edited form as: Nat Chem. 2010 May 23;2(8):638–643. doi: 10.1038/nchem.665

Figure 3. The design of a convergent coupling reaction suitable for the stereoselective synthesis of complex skipped polyenes.

Figure 3

a, Cope rearrangement of cis-divinylcyclopropanes. b, 1,5-hydrogen migrations in cis-vinylcyclopropanes. c, A plausible 6-electron process for acyclic 1,4-diene synthesis – alkene geometry is set as a function of the stereochemistry of the intermediate and the mechanistic course of the fragmentation. d, Design of a cross-coupling/fragmentation cascade for preparation of stereodefined skipped polyenes. Inline graphic = stereochemistry of up to three alkenes is established; Inline graphic = this carbon–carbon bond forming process has the potential to establish 1,4-dienes bearing a central stereodefined C3-carbon; Inline graphic = carbon–carbon bond formed in Ti-mediated cross-coupling; M = metal.