A new, non-iterative method for the asymmetric synthesis of long-chain and polycyclic polypropanoate fragments starting from 2,2′-ethylidenebis[3,5-dimethylfuran] (2) has been developed. Diethyl (2E,5E)-4-oxohepra-2,5-dienoate (6) added to 2 to give a single meso-adduct 7 containing nine stereogenic centers. Its desymmetrization was realized by hydroboration with (+)-IpcBH2 (isopinocampheylborane), leading to diethyl (1S,2R,3S,4S,4aS,7R,8R,8aR,9aS,10R,10aR)-1,3,4,7,8,8a,9,9a-octahydro-3 -hydroxy-2,4,5,7,10-pentamethyl-9-oxo-2H-10H-2.4a:7.10a-diepoxyanthracene -1,8-dicarboxylate ((+)-8: 78% e.e.). Alternatively, 7 was converted to meso-(1R,2R,4R,4aR,5S,7S,8S,8aR,9aS,10s,10aS)-1,8-bis(acetoxymethyl) -1,8,8a,9a-tetrahydro-2,4,5,7,10-pentamethyl-2H-10H-2.4a:7.10a -diepoxyanthracene-3,6,9(4H,5H,7H)-trione (32) that was reduced enantioselectively by BH3 catalyzed by methyloxazaborolidine 19 derived from L-diphenylprolinol giving (1S,2S,4S,4aS,5S,6R,7R,8R,8aS,9aR,10R,10aS)-1,8-bis(acetoxymethyl) -1,8,8a,9a-tretrahydro-6-hydroxy-2,4,5,7,10-pentamethyl-2H,10H-2.4a:7.10a -diepoxyanthracene-3,9(4H,7H)-dione ((-)-33: 90% e.e.). Chemistry was explored to carry out chemoselective 7-oxabicyclo[2,2,1]heptanone oxa-ring openings and intra-ring C-C bond cleavage. Polycyclic polypropanoates such as (1R,2S,3R,4R,4aR,5S,6R,7S,8R,9R,10R,11S,12aR)-1-(ethoxycarbonyl) -1,3,4,7,9,10,11,12,12a-decahydro-3,11-dihydroxy-2,4,5,7,9-pentamethyl-12 -oxo-2H,5H-2,4a:6,9:6,11-triepoxybenzocyclodecene-10,8-carbolactone (51). (1S,2R,3R,4R,4aS,5S,7S,8R,9R,10R,12S,12aS)-1,10-bis(acetoxymethyl) tetradecahydro-8-(methoxymethoxy)-2,4,5,7,9-pentamethyl-3,9-bis ([2-(trimethylsilyl)ethoxy]methoxy)-6,11-epoxycyclodecene-4a,6,11,12-tetrol ((+)-83), and (1R,2R,3R,4aR,4bR,5S,6R,7R,8R,8aS,9S,10aR)-3,5-bis(acetoxymethyl) -4a,8a-dihydroxy-1-(methoxymethoxy)-2,6,8,9,10a-pentamethyl-2,7-bis ([2-(trimethysilsyl)ethoxy]methoxy)dodecahydrophenanthrene-4,10-dione (85) were obtained in few synthetic steps.