Jaeyoung Ko1, Tadeusz F Molinski. 1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Abstract
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.
A five-step transformation of n class="Chemical">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 mammalianD-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.
Authors: Miriam H Kossuga; John B MacMillan; Evan W Rogers; Tadeusz F Molinski; Gislene G F Nascimento; Rosana M Rocha; Roberto G S Berlinck Journal: J Nat Prod Date: 2004-11 Impact factor: 4.050
Authors: Tatyana N Makarieva; Pavel S Dmitrenok; Alexander M Zakharenko; Vladimir A Denisenko; Alla G Guzii; Ronghua Li; Colin K Skepper; Tadeusz F Molinski; Valentin A Stonik Journal: J Nat Prod Date: 2007-12-06 Impact factor: 4.050