Total Syntheses of (±)-(Z)- and (±)-(E)-9

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into (3S*,5S*)-3,5-dimethyl-4-acetylcyclohexanone by
treating with TBAF in THF. Given with the fixed trans
relationship between the C-4 acetyl and C-3 methyl groups,
the relative steric relationships between the C-5 methyl and
the C-4 acetyl groups could be deduced from the coupling
constants of C-4 methine proton at d = 2.72 (dd, J=9.1, 3.7
Hz) from the 1 H NMR spectrum (see Supporting
Information).
Synthesis 2011, No. 5, 715–722 © Thieme Stuttgart · New York
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