In conclusion, a completely synthetic approach, not wedded to semi-synthesis, towards the scalable synthesis of calcipotriol and related analogs is described. Several steps are worth noting: 1) symmetry recognition to scalably access the A-ring via an unprecedented enantiocontrolled conjugate borylation of a cyclohexadienone; 2) strategic application of radical retrosynthesis for the rapid development of the CD ring using recently developed methods such as Ag-nanoparticle enabled electrochemical reductive cross coupling and a highly diastereoselective HAT-mediated annulation; 3) implementation of a semi-pinacol rearrangement to address the thermodynamically unfavored 6,5-trans ring fusion; 4) modular access to medicinally relevant analogs bypassing the need for a custom route for each derivative that is again reliant on Ag-nanoparticle electrochemical reductive cross coupling; and 5) scalability of routes to key fragments 47 and 22 via inexpensive starting materials without the need of any cryogenic temperatures. This modern take on the synthesis of a classic molecule (Vitamin D) builds on the rich history of prior syntheses and provides uniquely efficient access to both natural and unnatural analogs for exploration in medicine.