Plant derived diterpenoids are relevant as pharmaceuticals, food additives and fragrances, yet a broader industrial utilization of these bioproducts is limited due to their low natural abundance and high structural complexity. Mimicking the modularity of diterpene biosynthesis in plants, we constructed 51 functional diterpene synthase combinations, 41 of which were “new-to-nature”. Here, we demonstrate stereoselective biosynthesis in Nicotiana benthamiana of 47 diterpene skeletons including natural variants and novel enantiomeric or diastereomeric counterparts. Scalable biotechnological production for four selected industrially relevant targets was realized in engineered strains of Saccharomyces cerevisiae