Vinigrol is a novel diterpenoid isolated from a soil fungus, Virgaria nigra. From a medicinal point of view, vinigrol is of interest due to demonstrated antihypertensive and platelet-inhibiting properties. Additionally, it has been discovered to act as a tumor necrosis factor antagonist, halting the progression of AIDS-related complex to AIDS, and nerve stem cell proliferation promoter. Given the combination of a structurally unique, synthetically challenging carbon framework and potential pharmaceutical applications, our interest lies in the total synthesis of vinigrol. Synthetic strategies employing oxidative dearomatization and intramolecular DielsAlder cycloaddition are used to access structures towards this intriguing molecule.