Search

Intramolecular reductive coupling of the bis-aldehyde(14) in the presence of Ti(0), followed by 1,4-reduction of the resulting tetraene(16) using sodium in ammonia, provides a facile synthesis of E , E -verticillene(2), the putative biogenetic precursor of the taxane family of alkaloids e.g. (3).

Treatment of either the verticillenes (3), (6), (13) or (14) with Lewis acids fails to produce the corresponding taxane carbon framework viz (2), and instead only products, e.g. (8), (9), (16), of rearrangement of the epoxide rings in the substrates are obtained.