1417142-06-3Relevant academic research and scientific papers
D-glucosamine-derived synthons for assembly of l - Threo -sphingoid bases. Total synthesis of rhizochalinin C
Ko, Jaeyoung,Molinski, Tadeusz F.
, p. 498 - 505 (2013/02/25)
A five-step transformation of d-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of l-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, two-headed sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.
