Ras proteins are subjected to posttranslational farnesylation at a cysteine the fourth residue from the C-terminus, in which protein farnesyltransferase (PFTase) is concerned. Andrastins A-D are unique meroterpenoids (mixed polyketide-terpenoid) and novel protein farnesyltransferase inhibitors. Since farnesylation is essential for the transforming activity of mutated Ras proteins, andrastins are expected to be promising antitumor agents. Andrastins were found from the cultured broth of Penicillium sp. FO-3929 by Omura and co-workers in 1996. The novel tetracyclic carbon skeletons of these meroterpenoids having six or seven stereogenic centers and an angularly disubstituted perhydrobenzo[e]indene moiety, comprise the B, C and D rings. Although their unusual structures and biological activities have made them the subject of intense synthetic interest, the total synthesis of andrastins has not yet been reported probably due to their structural complexity. In this paper, we describe efficient and general methods for the syntheses of the perhydrophenanthrene (ABC ring system) and the fully functionalized perhydrobenzo[e]indene (BCD ring system) of andrastins A-D. Both sytheses commence from Wieland-Miescher ketone, and the former features intramolecular Diels-Alder raction and the latter is characterized by using a Ti(III)-mediated radical cyclization or an ene reaction. These reactions were successfully applied to the constructions of the both ring systems.