We designed spirotricyclic ureas 2a-c bearing structurally and electronically-diverse N-urea substituents as our basic building blocks for scaffold elaboration (note: throughout, the suffixes a, b and c refer to structures bearing 2-propyl, 4-methoxyphenyl and p-toluenesulfonyl substituents respectively). The requisite ureas were prepared using our previously-developed oxidative dearomatisation using the corresponding hydroxyphenyl ureas 1a-c (see Supporting Information), Scheme 1. Although the oxidative dearomatisation reactions were moderate yielding, the short nature of the synthetic route allowed ready supply of material for further study. Before moving on to scaffold diversification, we demonstrated functionalisation of the enone functionality in the spirotricyclic ureas. Chemo-and stereoselective reduction to allylic alcohol was achieved under Luche conditions, giving a single diastereomer 3a, whose stereochemistry was determined crystallographically. Enones 2a-c could be reduced to the saturated derivatives 4a-c in excellent yield either by rhodiumcatalysed conjugate reduction with triethylsilane or by hydrogenation over Pd(OH)2/C. Nucleophilic addition to the resulting ketones was also highly stereoselective: addition of a Grignard reagent to 4a gave a single diastereomeric alcohol 5a, while reduction could be most effectively achieved using sodium borohydride with added cerium(III) chloride, again giving a single diastereomeric product 6a (use of lithium aluminium hydride was both lower yielding and less selective). Reductions of 4b and 4c were similarly high-yielding but slightly less selective. Finally, stereoselective conversion to the secondary amine 7aa was best achieved by pre-formation of the corresponding imine and reduction with sodium borohydride, giving an 88:12 mixture of disastereomers. The stereochemistry of alcohol 6a and amine 7a was unambiguously determined by X-ray crystallography of suitable derivatives (see Supporting Information). Analysis of crystal structures of the saturated ketones 4b and 4c (Supporting Information) shows that they adopt boat-like conformations about the cyclohexanone ring: the stereochemical outcome of the addition reactions is consistent with attack on the less-hindered exocyclic face of the carbonyl or derived imine.