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Various aspects of stereoselective synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines with the use of natural compounds as chirality sources are reviewed. The following low molecular weight substrates are considered: carbohydrates, isoprenoids, hydroxyacids, alkaloids and amino acids. Examples of various synthetic methodologies that employ the above derivatives as chiral building blocks, chiral auxiliaries or chiral ligands are presented.