Total Synthesis of Amphidinolide E

• Abstract
• Full Text HTML
• Hi-Res PDF[69 KB]
• PDF w/ Links[160 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF₃·Et₂O promoted [3+2] annulation reaction between aldehyde 3 and allylsilane 4 to afford substituted tetrahydrofuran 2.

Citing Articles

View all 44 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 15 ACS Journal articles (5 most recent appear below).

• 

  Ring Strain-Promoted Allylic Transposition of Cyclic Silyl Ethers

  Ivan Volchkov, Sangho Park, and Daesung Lee
  Organic Letters2011 13 (13), 3530-3533

  • Ring Strain-Promoted Allylic Transposition of Cyclic Silyl Ethers

    Ivan Volchkov, Sangho Park, and Daesung Lee
    Organic Letters2011 13 (13), 3530-3533

    Relief of the ring strain of medium-sized rings promotes a regioselective allylic transposition of a C–O bond when catalyzed by rhenium oxide. Through the allylic transposition, eight-membered cyclic silyl ethers undergo ring contraction to the ...

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

  Total Synthesis of Malyngamides K, L, and 5′′-epi-C and Absolute Configuration of Malyngamide L

  Jun-Tao Zhang, Xian-Liang Qi, Jie Chen, Bao-Sheng Li, You-Bai Zhou, and Xiao-Ping Cao
  The Journal of Organic Chemistry2011 76 (10), 3946-3959

  • Total Synthesis of Malyngamides K, L, and 5′′-epi-C and Absolute Configuration of Malyngamide L

    Jun-Tao Zhang, Xian-Liang Qi, Jie Chen, Bao-Sheng Li, You-Bai Zhou, and Xiao-Ping Cao
    The Journal of Organic Chemistry2011 76 (10), 3946-3959

    An accelerated, enantioselective, and general synthetic route to a class of malyngamides, K (1), L (3), and 5′′-epi-C (4), bearing a cyclohexenone ring or a heavily oxygenated six-membered ring and a vinyl chloride structural motif was developed. The key ...

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

  Enantioselective Syntheses of syn- and anti-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions

  Ming Chen and William R. Roush
  Organic Letters2011 13 (8), 1992-1995

  • Enantioselective Syntheses of syn- and anti-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions

    Ming Chen and William R. Roush
    Organic Letters2011 13 (8), 1992-1995

    The kinetic hydroboration of allenylsilane 5 with (dIpc)2BH at −40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above −40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >...

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

  Desymmetrization of (R,R)-Hexa-1,5-diene-3,4-diol via Monofunctionalization and Rhodium-Catalyzed Allylic Substitution

  Bernd Schmidt and Lucia Staude
  The Journal of Organic Chemistry2011 76 (7), 2220-2226

  • Desymmetrization of (R,R)-Hexa-1,5-diene-3,4-diol via Monofunctionalization and Rhodium-Catalyzed Allylic Substitution

    Bernd Schmidt and Lucia Staude
    The Journal of Organic Chemistry2011 76 (7), 2220-2226

    A sequence of selective monoprotection and Rh-catalyzed enantioconservative allylic substitution is established as a desymmetrization strategy for C2-symmetric hexa-1,5-diene-3,4-diol. A benzyl protecting group and ethyl carbonate as a leaving group ...

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

  Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level

  Soo Bong Han, Xin Gao and Michael J. Krische
  Journal of the American Chemical Society2010 132 (26), 9153-9156

  • Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level

    Soo Bong Han, Xin Gao and Michael J. Krische
    Journal of the American Chemical Society2010 132 (26), 9153-9156

    Using the ortho-cyclometalated π-allyl iridium precatalyst (R)-I derived from [Ir(cod)Cl]2, 4-cyano-3-nitrobenzoic acid, (R)-SEGPHOS, and allyl acetate, enantioselective transfer hydrogenation of α-(trimethylsilyl)allyl acetate in the presence of ...

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

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing