
%0 Journal Article
%A Banwell, MG 
%A Cowden, CJ 
%A Gravatt, GL 
%A Rickard, CEF 
%T Synthesis of the Troponoid Natural Product Nezukone Via Sequential Rearrangement of Two Isomeric Precursors
%J Australian Journal of Chemistry
%D 1993/12/01
%V 46
%N 12
%P 1941-1954
%K 
%R https://doi.org/10.1071/CH9931941
%U https://www.publish.csiro.au/paper/CH9931941 
%X Nezukone (1) has been synthesized in seven steps from the readily available &#916;3-trinorcarene (4). Key features of the sequence used include formation of the bicyclic isomer (2) of compound (1). Base-promoted isomerization of compound (2) followed by acidic workup then produced the isolable but highly unstable heptafulvenol (3), an extended enolic  tautomer of nezukone (1). Under mildly basic conditions compound (3) rearranged to give the natural product (1). The X-ray crystal structure of the ring-fused cyclobutanone (8) is reported. 
