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Cryptomoscatones D1 and D2, dihydropyranones isolated from C. mandiocanna, had their stereochemistry solved after total syntheses and comparison of spectroscopic data of natural and synthetic samples. Natural dihydropyranones coibacins A and B, metabolites isolated from marine cyanobacterium cf. Oscillatoria sp, which display antileishmanial activity and anti-inflammatory properties, were synthesized and had their absolute configuration determined. Our efforts towards the synthesis of cryptomoscatone E3, natural dihydropyranone with unknown absolute configuration, are also discussed.