Synthesis of a Furanosyl‐pyranone Derivative Related to the Tri‐O‐heterocyclic Core of Herbicidins

A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels—Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.

[1]  S. Hung,et al.  Deuterium-isotope study on the reductive ring opening of benzylidene acetals. , 2011, Organic & biomolecular chemistry.

[2]  U. Ellervik,et al.  Regioselective reductive openings of 4,6-benzylidene acetals: synthetic and mechanistic aspects. , 2011, Carbohydrate research.

[3]  Fernando Sartillo‐Piscil,et al.  High 1,3-trans stereoselectivity in nucleophilic substitution at the anomeric position and β-fragmentation of the primary alkoxyl radical in 3-amino-3-deoxy-ribofuranose derivatives: application to the synthesis of 2-epi-(-)-jaspine B. , 2011, The Journal of organic chemistry.

[4]  S. Hung,et al.  Metal Trifluoromethanesulfonate-Catalyzed Regioselective Reductive Ring Opening of Benzylidene Acetals , 2009 .

[5]  Jinq-chyi Lee,et al.  Regioselective one-pot protection of carbohydrates , 2007, Nature.

[6]  S. Hung,et al.  Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals. , 2005, Angewandte Chemie.

[7]  D. Bonnaffé,et al.  Efficient Preparation of Three Building Blocks for the Synthesis of Heparan Sulfate Fragments: Towards the Combinatorial Synthesis of Oligosaccharides from Hypervariable Regions , 2003 .

[8]  Ching-Yun Hsu,et al.  Studies on the Regioselective Reductive Ringcleavage Reactions of 3,5-O-Arylidene- d-xylofuranosides , 2003 .

[9]  S. Shuto,et al.  The First Synthesis of Herbicidin B. Stereoselective Construction of the Tricyclic Undecose Moiety by a Conformational Restriction Strategy Using Steric Repulsion between Adjacent Bulky Silyl Protecting Groups on a Pyranose Ring , 1999 .

[10]  E. Perrin,et al.  Synthesis of the Carbon Skeleton of the Herbicidins via a Temporary Silaketal Tether , 1996 .

[11]  T. Gallagher,et al.  Carbohydrate building blocks in heterocyclic chemistry. Synthetic studies directed towards the herbicidins , 1996 .

[12]  P. Vogel,et al.  Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs , 1995 .

[13]  E. Larson,et al.  On the scope, mechanism and stereochemistry of the Lewis acid catalyzed cyclocondensation of activated dienes with aldehydes: an application to the erythronolide problem , 1985 .

[14]  J. Springer,et al.  Chelation-controlled facially selective cyclocondensation reactions of chiral alkoxy aldehydes: syntheses of a mouse androgen and of a carbon-linked disaccharide , 1985 .

[15]  H. Kuwano,et al.  The revised structure of herbicidins. , 1982, The Journal of antibiotics.

[16]  H. Yoshikawa,et al.  Herbicidins F and G, two new nucleoside antibiotics. , 1979, The Journal of antibiotics.

[17]  H. Yoshikawa,et al.  Herbicidins C and E, two new necleoside antibiotics. , 1979, The Journal of antibiotics.

[18]  T. Haneishi,et al.  Herbicidins A and B, two new antibiotics with herbicidal activity. I. Producing organism and biological activities. , 1976, The Journal of antibiotics.

[19]  A. Terahara,et al.  Herbicidins A and B, two new antibiotics with herbicidal activity II. Fermentation, isolation and physico-chemical characterization. , 1976, The Journal of antibiotics.

[20]  Jinq-chyi Lee,et al.  Regioselective one-pot protection of glucose , 2008, Nature Protocols.

[21]  S. Shuto,et al.  Convergent synthesis of adenophostin A analogues via a base replacement strategy , 2000 .

[22]  T. Gallagher,et al.  Studies directed towards the synthesis of herbicidins. Model study based on late stage N-glycosylation , 1996 .

[23]  D. A. Whiting,et al.  Short synthetic route to congeners of the undecose antibiotic herbicidin , 1995 .