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Abstract

The total syntheses of the two aryl C-glycoside natural products diospongins A and B are described. The key reactions involved stereoselective reductions of the appropriate oxocarbenium cations that were derived from a common δ-lactone intermediate.

Citing Articles

View all 22 citing articles

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This article has been cited by 9 ACS Journal articles (5 most recent appear below).

• 

  A Formal Synthesis of (−)-Cyanolide A Featuring a Stereoselective Mukaiyama Aldol Reaction and Oxocarbenium Reduction

  Robert J. Sharpe and Michael P. Jennings
  The Journal of Organic Chemistry2011 76 (19), 8027-8032

  • A Formal Synthesis of (−)-Cyanolide A Featuring a Stereoselective Mukaiyama Aldol Reaction and Oxocarbenium Reduction

    Robert J. Sharpe and Michael P. Jennings
    The Journal of Organic Chemistry2011 76 (19), 8027-8032

    The formal synthesis of the marine natural product (−)-cyanolide A is presented. The synthetic strategy is centered on two acyclic diastereoselective reactions and a single cyclic reaction with modest to excellent dr based on an initial stereocenter. Most ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Formal Synthesis of (−)-Neopeltolide Featuring a Highly Stereoselective Oxocarbenium Formation/Reduction Sequence

  Dionicio Martinez-Solorio and Michael P. Jennings
  The Journal of Organic Chemistry2010 75 (12), 4095-4104

  • Formal Synthesis of (−)-Neopeltolide Featuring a Highly Stereoselective Oxocarbenium Formation/Reduction Sequence

    Dionicio Martinez-Solorio and Michael P. Jennings
    The Journal of Organic Chemistry2010 75 (12), 4095-4104

    The formal synthesis of the unnatural (−)-neopeltolide core is discussed in detail. Efficient application of the Evans’ protocol for the synthesis of 1,3-syn-diols via an intramolecular hetero-Michael addition followed by reductive deprotection of the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Facile and Efficient Synthesis of 4-Hydroxy-2,6-cis-tetrahydropyrans via Tandem Cross-Metathesis/Thermal S_N2′ Reaction: Protecting-Group-Free Synthesis of (±)-Diospongin A

  Kiyoun Lee, Hyoungsu Kim and Jiyong Hong
  Organic Letters2009 11 (22), 5202-5205

  • A Facile and Efficient Synthesis of 4-Hydroxy-2,6-cis-tetrahydropyrans via Tandem Cross-Metathesis/Thermal S_N2′ Reaction: Protecting-Group-Free Synthesis of (±)-Diospongin A

    Kiyoun Lee, Hyoungsu Kim and Jiyong Hong
    Organic Letters2009 11 (22), 5202-5205

    The tandem cross-metathesis/thermal SN2′ reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Trans-2,5-Disubstituted Tetrahydrofurans via Addition of Carbon Nucleophiles to the Strained Bicyclic Acetal 2,7-Dioxabicyclo[2.2.1]heptane

  Gregory K. Friestad and Hye Jin Lee
  Organic Letters2009 11 (17), 3958-3961

  • Trans-2,5-Disubstituted Tetrahydrofurans via Addition of Carbon Nucleophiles to the Strained Bicyclic Acetal 2,7-Dioxabicyclo[2.2.1]heptane

    Gregory K. Friestad and Hye Jin Lee
    Organic Letters2009 11 (17), 3958-3961

    Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl4 produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  An Efficient Formal Synthesis of (−)-Clavosolide A Featuring a “Mismatched” Stereoselective Oxocarbenium Reduction

  Jesse D. Carrick and Michael P. Jennings
  Organic Letters2009 11 (3), 769-772

  • An Efficient Formal Synthesis of (−)-Clavosolide A Featuring a “Mismatched” Stereoselective Oxocarbenium Reduction

    Jesse D. Carrick and Michael P. Jennings
    Organic Letters2009 11 (3), 769-772

    The enantioselective formal synthesis of the polyketide marine natural product (−)-clavosolide A is presented. The construction of the β-C-glycoside subunit is highlighted by a one-pot oxocarbenium cation formation/reduction sequence. Yamaguchi ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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