(both racemic and enantioselective) to 1 featuring a number of unconventional tactics and a strategy relying on skeletal reorganization to precisely install the key ring systems (Scheme 1). Several generations of retrosynthetic analyses were applied resulting in a successful solution to this puzzle. In the initial design, an ambitious approach wherein a simple linear intermediate would undergo a series of self-condensations controlled by a single methyl-containing stereocenter was pursued (Gen. 1, Figure ). Unfortunately, the polarity of intermediates and difficulty in controlling the reactivity of such compounds proved unfeasible. Next, a "two-phase" strategy 5 was investigated through the sequential amination of a simple polyunsaturated decalin (Gen. 2). This path, however, resulted in a linear route stymied by functionalization challenges (regio-and stereo-selectivities). The learnings from these two excursions led to a third design plan aiming to annulate multiple rings from a central B-ring precursor (Gen. 3). This plan also faltered due to improper control of stereochemistry and C-N bond forming steps that would not proceed. The final successful route to 1 hinged upon a more convergent design that implemented the lessons of prior approaches and addressed stereochemical and chemoselectivity issues 6 with exquisite control.