A novel approach for the synthesis of 13a-methyl tylophora alkaloids has been reported. The key features included two different synthetic pathways targeted at transforming the β-nitro-azabicycle to the phenanthrene core. The successful steps involved the oxidation of the nitro-piperidine moiety to the corresponding α,β-unsaturated ketone, and an oxidative biaryl coupling reaction for phenanthrene ring formation. Finally, the desired product was obtainedviaa formal reductive removal of the hydroxyl group. This methodology has been applied for the synthesis of 13a-methyl tylophora alkaloids in up to 65% yield over six steps from β-nitro-azabicycles. Both natural and unnatural enantioenriched hypoestestatins 1 and 2, and related compounds were synthesized using parallel kinetic resolution of the CBS-oxazaborolidine-catalyzed reduction of racemic ketones to provide two separable diastereomeric alcohols in combined yields up to 91% and with high enantioselectvity (up to 89% ee). In addition, the catalytic asymmetric reduction toseco-hypoestestatins 1 and 2 has been reported for the first time. Thus, the ability to develop the racemic mixtures to both enatioenriched forms offers benefit for various biological assays in the future. © The Royal Society of Chemistry 2021.