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We have synthesised unsaturated AE-bicyclic analogues of lycoctonine class norditerpenoid alkaloids by acetylide addition and regiochemically controlled reductions. Reduction of a substituted propargylic alcohol with hydrogen gas (poisoned Pd catalyst) gave an alkene with vicinal J = 13.5 Hz. This was shown to be of Z-geometry by unambiguously preparing the corresponding E-alkene (J = 15.4 Hz).

Original publication

DOI

10.1016/S0040-4039(97)10649-9

Type

Journal article

Journal

Tetrahedron Letters

Publication Date

19/02/1998

Volume

39

Pages

893 - 896