Skeletal remodeling of 11 also supported entry to unprecedented abeo-abietane scaffolds (Scheme 5). For example, exposure of 11 to BF 3 •OEt 2 in toluene at 80 °C afforded isomeric [6-7-6] ring system 19 in 95% yield. We suspect that that 19 is derived of cation A, which itself arises from a (net) [1,3]alkyl shift within the initial Lewis adduct of 11. Alternatively, irradiation of 11 (hv = 254 nm) in the presence of Et 3 N generated [4.4.1] bicyclic motif 20, putatively via ketyl radical B. This carbocycle is reminiscent of the cyclocitrinols, and was available at a higher oxidation state from 10. In this case, 10 was reacted with NIS in aqueous THF to give halohydrin C. Upon exposure to Ag(TFA), this reactive species furnished alcohols 21 and 22 in 82% yield (1:1 ratio). We found that 21 isomerized to 22 in the presence of TsOH, putatively via cation D. Alternatively, 22 was isolated in 82% yield when MeCN was used in place of THF. Collectively, these non-canonical abietanes illustrate the structural diversity that can be achieved by controlled fragmentation of the propellane within 5a.