Literature DB >> 23227909

D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.

Jaeyoung Ko1, Tadeusz F Molinski.   

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.

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Year:  2012        PMID： 23227909      PMCID： PMC3548972          DOI： 10.1021/jo302355t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  26 in total

1.  (-)-Rhizochalin is a Dimeric Enantiomorphic (2R)-Sphingolipid: Absolute Configuration of Pseudo-C(2v)-Symmetric Bis-2-amino-3-alkanols by CD We thank Jeff de Ropp and John MacMillan (University of California, Davis) for assistance with the 600 and 400 MHz (1)H NMR spectra, respectively; Gillian Nicholas (University of California, Davis) for measurement of the CD spectra of 7 a, b; Rich Kondrat (University of California, Riverside Mass Spectrometry Facility) for chemical ionization MS; and Carlito Lebrilla and Yongming Xie (University of California, Davis) for matrix-assisted laser desorption/ionization MS. This work was supported by the National Institutes of Health (NIH; grant no. AI 39987). The NMR spectrometers were funded in part by the National Science Foundation (grant no. CHE-9808183; 400 MHz apparatus) and the NIH (grant no. RR11973; 600 MHz apparatus). CD=circular dichroism.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-17       Impact factor: 15.336

2.  (2S,3R)-2-aminododecan-3-ol, a new antifungal agent from the ascidian Clavelina oblonga.

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

3.  Synthesis of the glycosphingolipid beta-galactosyl ceramide and analogues via olefin cross metathesis.

Authors:  Anand Narain Rai; Amit Basu
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

4.  Novel marine sponge amino acids, 10. Xestoaminols from Xestospongia sp.

Authors:  C Jiménez; P Crews
Journal:  J Nat Prod       Date:  1990 Jul-Aug       Impact factor: 4.050

5.  (2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the caribbean sponge Haliclona vansoesti.

Authors:  C Devijver; M Salmoun; D Daloze; J C Braekman; W H De Weerdt; M J De Kluijver; R Gomez
Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

6.  Total synthesis and biological evaluation of structural analogues of compactin and dihydromevinolin.

Authors:  C H Heathcock; C R Hadley; T Rosen; P D Theisen; S J Hecker
Journal:  J Med Chem       Date:  1987-10       Impact factor: 7.446

7.  An efficient and highly stereocontrolled route to bulgecinine hydrochloride.

Authors:  Juhienah K Khalaf; Apurba Datta
Journal:  J Org Chem       Date:  2004-01-23       Impact factor: 4.354

8.  Structure elucidation at the nanomole scale. 1. Trisoxazole macrolides and thiazole-containing cyclic peptides from the nudibranch Hexabranchus sanguineus.

Authors:  Doralyn S Dalisay; Evan W Rogers; Arthur S Edison; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2009-04       Impact factor: 4.050

9.  Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in alpha,omega-bifunctionalized ketosphingolipids.

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

Review 10.  Sphingosine kinase inhibitors and cancer: seeking the golden sword of Hercules.

Authors:  Susan Pyne; Robert Bittman; Nigel J Pyne
Journal:  Cancer Res       Date:  2011-09-22       Impact factor: 12.701
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  1 in total

Review 1.  Secondary Metabolites from Marine Sponges of the Genus Oceanapia: Chemistry and Biological Activities.

Authors:  Meng-Juan Xu; Lin-Jing Zhong; Jun-Kun Chen; Qing Bu; Lin-Fu Liang
Journal:  Mar Drugs       Date:  2022-02-16       Impact factor: 5.118
  1 in total

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