Publisher Summary Sphingosines are a related class of long chain aliphatic compounds possessing a 2-amino-1,3-diol moiety. The most common member of this group found in nature is (2S,3R)- D - erythro -2-amino-1,3-octadec-4E-enediol 1a and is frequently referred to as “sphingosine.” These molecules are the backbone of more complex sphingolipids, including ceramide, sphingomyelin, cerebrosides, and glycosphingolipids. Ubiquitous to all living organisms, sphingolipids play many biologically important roles. There have been many published syntheses of sphingosine and its derivatives in the literature since the first reported sphingosine synthesis by Shapiro, with each synthesis offering something unique. Some syntheses utilize inexpensive starting materials from the chiral pool, whereas others control stereochemistry through asymmetric induction. High yield and few steps may be the hallmark of some preparations, whereas synthetic elegance, stereoselectivity, or the ability to convert to other sphingolipids or natural products may be the attributes of others. Because of this wealth of approaches, chemists have choices for the preparation of synthetic sphingoid bases, but determining which procedure to use depends on the researcher's specific needs. This chapter discusses many protocols, provides insights about each preparation, and facilitates the selection of sphingolipid synthetic preparations. Sphingosine syntheses can be divided into several categories. Syntheses that start from chiral precursors are divided into those that begin with serine derivatives and those that begin with sugar derivatives. Syntheses that utilize asymmetric epoxidations, aldol reactions, and relevant miscellaneous methods constitute the remaining sections.