In the context of target-oriented chemical synthesis, only three total syntheses of trans-syn-fused drimane terpenoids have been reported thus far (Figure ). Two of these syntheses pertain the brasilicardin natural products and involved lengthy synthetic sequences to generate the key trans-syn-trans-fused tricyclic intermediates. More recently, a landmark synthesis of the isomalabaricanes (e.g., stellettin E, 5) by the Sarlah group has enabled initial structure-activity relationship studies on the cytotoxicity of the scaffold. To complement the aforementioned approaches, we sought to develop an alternative strategy to collectively prepare trans-syn-fused drimane meroterpenoids through the use of a chiral pool approach. This report discloses the development of a unified strategy to access both trans-syn-cisand trans-syn-trans-fused drimane meroterpenoids from sclareolide that culminates in the first total syntheses of polysin, N-acetyl-polyveoline, chrodrimanin C and verruculide A. To the best of our knowledge, this is the first reported de novo constructions of trans-syn-cis-fused perhydrobenz[e]indene and trans-syn-trans-fused dodecahydro-1Hbenzo[f]chromene frameworks. This work was made possible by the use of an underexplored epimerization reaction on sclareolide, which was combined with enzymatic C-H oxidations and efficient ring annulations to complete the divergent syntheses. We anticipate that the strategy delineated herein will find a broad range of applications in the preparation of other drimane terpenoids with unusual ring fusions.