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Sesame lignans, whose biosynthetic pathway is the subject of this study, have well-established antioxidant and health protecting properties. Using a combination of radio- and stable-isotopically labelled precursor administration experiments, it was demonstrated that E-coniferyl alcohol undergoes stereoselective coupling to afford (+)-pinoresinol in Sesamum indicum seeds. Only this enantiomer, and not its (−)-antipode, is metabolized further in maturing seeds to afford (+)-piperitol, (+)-sesamin, and (+)-sesamolin. Introduction of the methylene dioxy bridges occurs sequentially with piperitol first being formed, this being subsequently modified to afford sesamin.