Aquilanols A (1) and B (2) are naturally occurring sesquiterpenoids, isolated by Park et al., in 2017 from the agarwood of Aquilaria malaccensis (Figure ). Their intriguing structure comprises a 7/10 bicyclic skeleton, unprecedented within the humulene-type sesquiterpenoids family. The inherent strain of such medium-sized bicyclic frameworks is further intensified by the presence of a double bond on the junction of the two rings and a trans-disubstituted double bond incorporated into the 10membered ring. Although, preliminary evaluation did not reveal any significant activity when tested against certain Grampositive and Gram-negative bacteria, such strained molecular scaffolds hold high potential for biological activity, owned to strain-releasing-driven reactivity. This expectation is supported by the fact that agarwood is produced by the plant in response to microbials infections. Given the interest of our group in the synthesis of small-molecular weight antibacterial agents, 3 combined with the challenging structural features of aquilanols A and B, we embarked on the synthesis of the abovementioned compounds. Our interest became ever greater on the notice that no total synthesis has been reported so far and that price of agarwood, the natural source of aquilanols, is exceptional high and keeps rising due to emerging depletion of the Aquilaria tree population. On a first thought in designing of our synthetic plan, we wished to probe the viability of the biosynthetic hypothesis suggested by Park and co-workers. According to their proposal, aquilanol A (1) was derived from an intramolecular epoxide opening event on a highly oxidized derivative of humulene (3) (Figure , compound 4). Consequently, our initial objective was oriented toward the assembly of the eleven-membered carbocyclic oxygenated intermediate 4. A blueprint of our approach towards this goal encompassed the construction of polyunsaturated precursor 8, upon which a ring closure metathesis would be applied to formulate the ring (Figure ). Albeit rare, such strategies for the preparation of eleven-membered carbocycles are reported in the literature. Unfortunately, this approach proved fruitless on our systems, despite several variations on the cyclisation substrate we attempted the reaction on. As often the case in terpene synthetic world, we turned our attention to terpene chiral pool to identify easily accessible natural compounds, that could serve as alternative starting materials to formulate the macrocyclic core. Our interest was attracted by (-)-caryophyllene oxide (11), a naturally derived material, available in large quantities and low cost (approx. 0,6 USD/g) and in acceptable purity (>95%). 8 Shenvi have recently demonstrated the high added-value conversion of the latter to much more precious humulene oxide (10), stereoselectively, via a radical retro-cycloisomerization reaction catalyzed by Co(III)salen species (Scheme 1). This transformation perfectly suited to the needs of our plan. A retrosynthetic analysis capitalizing on the latter would encompass only an additional regio-and stereospecific allylic oxidation on the pendent methyl group of the trisubstituted double bond in 10 (Scheme 1). Unfortunately, (-) -caryophyllene oxide, the only enantiomer commercially available, leads to the enantiomer of the natural compound, ent-aquilanol A (ent-1). Even so, we decided to test our hypothesis as it constitutes a rapid and versatile access to the broader family of aquilanols.