Semi synthesis of structurally interesting and highly oxygenated terpenoids from more simple and available starting materials is considered one of the main areas of investigation in natural product synthesis. In our research program we investigate intriguing reactions invoked in the biosynthesis and try to mimic those transformations in the laboratory. Target reactions include for example cascade polyene cyclisations (Greenwaylactams A-C), intramolecular aldol reactions (Alstoscholarinoids A-B, see Scheme 1) as well as cationic rearrangements (Forrestiacids A-B). Alstoscholarinoids A and B are triterpenoids with novel, rearranged carbon skeleta, which were first isolated in 2021 in extremely small quantities from the medicinal plant Alstonia scholaris. These terpenoids exhibit some intriguing biological activity (potent antihyperuricemic effects) and unique 6/6/5/6/6/6 and 6/6/6/7/5 ring systems and were therefore targeted for synthesis. The final steps in our retrosynthetic analysis were the “obvious” supposed biogenetic disconnections (purple) giving rise to key dialdehyde and 10-membered diketone. The reactions required to render the final natural products from these intermediates can suffer from some immediate selectivity issues (site of deprotonation, stereochemistry of addition) which we aimed to surpass by careful tuning of reaction conditions. In this light, the synthesis started from commercially available oleanolic acid and led to the required precursors in 5 or 8 steps longest linear sequence.