Tetrahedron p. 97 - 106 (1998)
Update date:2022-08-02
Topics:
Jenn, Thierry
Heissler, Denis
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.
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