Stereoselective synthesis of d-erythro- and l-threo-sphinganines via palladium-catalyzed equilibration and Suzuki coupling

Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

“…Literature syntheses of sphinganines are not as abundant as those for sphingosines (which have a double bond at C4 of the sphingoid base), although it is obvious that sphinganines are available in only one step from the corresponding sphingosines by reduction. Sphinganines have been synthesized from sugars, , from the amino acid, serine, − and from racemic precursors by a variety of asymmetric strategies. − In general, the most common and straightforward syntheses exploit serine derivatives, with routes from serine to the sphinganines generally being six or more steps. By contrast, our current approach to sphinganines 7 is a four-step, three-purification procedure from commercially available Boc-serine (Scheme ).…”

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

“…The major challenges associated with the synthesis of sphingoid bases involve setting the erythro stereochemistry and, for sphingosine in particular, setting the trans stereochemistry of the alkene . In general, erythro stereochemistry has been achieved from stereochemical starting materials, such as l -serine − or carbohydrates, − or from racemic intermediates using various asymmetric strategies. − Synthetic methods to access sphingoid bases have been thoroughly reviewed elsewhere. − …”

Stereoselective Synthesis of (−)‐Chloramphenicol, (+)‐Thiamphenicol and (+)‐Sphinganine via Chiral Tricyclic Iminolactone

“…[9][10][11] For example, the β-galactosyl ceramide, plakoside A, isolated from the marine sponge Plakortis simplex, was found to be a noncytotoxic immunosuppressant. [17][18][19][20][21][22][23][24][25][26][27] As part of our continuous work on the stereoselective synthesis of α-amino acid using chiral tricyclic iminolactone which is derived from natural (1R)-(＋)-camphor, [28][29][30][31][32][33][34][35][36][37] we successfully developed a concise and effective methodology to synthesize optically pure β-hydroxy-α-amino acid. [14,15] However, it is not an easy task to synthesize glycosphingolipids for extensive research purpose.…”