Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl-2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of $190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen–Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy)benzaldehyde used in the Claisen–Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η⁵-formylcyclopentadienyl)(η⁴-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C–C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert-butyl tert-butanethiosulfinate with benzyllithium derivatives, obtained by deprotonation of the corresponding toluene derivatives, gave a wide variety of benzyl tert-butyl sulfoxides with complete inversion of configuration. The benzyl sulfoxides were deprotonated in situ, and addition of the electrophiles gave α-substituted products with good diastereoselectivity.

The Birch reduction of hexaphenylbenzene yields two isomers of 1,2,3,4,5,6-hexaphenylcyclohexane. The X-ray crystal structure of the all-cis isomer, 1, reveals that the severe steric crowding among the three axial phenyls is alleviated by a marked splaying out of those three aryl substituents relative to the positioning in a conventional chair structure. A second product, 2, was identified crystallographically and by NMR spectroscopy as the 1,3-diaxial-2,4,5,6-tetraequatorial (epi) isomer of hexaphenylcyclohexane, in which only five of the six additional hydrogen atoms are positioned on the same face of the C₆Ph₆ precursor. A variable-temperature NMR study of the all-cis isomer 1 yielded a chair-to-chair inversion barrier of ≈19 kcal mol⁻¹, which is somewhat higher than the previously reported values for all-cis-1,2,3,4,5,6-C₆H₆R₆ in which R=Me or CO₂Me. The possible relevance to Cannizzaro's 1854 report of a product with the formula (C₇H₆)_n is discussed. By contrast, Birch reduction of pentaphenylbenzene led to the formation of 2,3,5,6-tetraphenyl-1,1′-bicyclohexylidene.