Synthesis of tricyclopolyprenols via a radical addition and a stereoselective elimination. Part I: Methodology

Article abstract of DOI:10.1016/S0040-4020(97)10259-9

The feasibility of a synthesis of tricyclopolyprenols based on the addition of the isocopalen-15-yl radical either to a 2-methylene-3-hydroxy alkenenitrile or to a methyl 2-methylene-3-hydroxy alkenoate - both prepared by a Baylis-Hillman reaction - is examined. When two model adducts, a β-acetoxy nitrile and a β-mesyloxy ester, were subjected to an elimination reaction, the former gave a trans α,β-unsaturated nitrile whereas the latter gave a cis α,β-unsaturated ester. The reduction of the ancillary cyano or methoxycarbonyl groups into a methyl is also described.