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Biomimetic Macrocycle-Forming Diels−Alder Reaction of an Iminium Dienophile: Synthetic Studies Directed Toward Gymnodimine
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Abstract
The macrocyclic core of gymnodimine has been constructed via an intramolecular Diels−Alder reaction of an α,β-unsaturated iminium dienophile in water. The cycloaddition furnished a single exo-product, along with two endo-products. Through X-ray analysis of a suitable derivative, the stereochemistry of the exo-product was established, thereby demonstrating that its stereochemistry matches that of gymnodimine. In contrast, macrocyclization of an analogous α,β-unsaturated ketone dienophile gave only undesired endo-products. Interestingly, the imine dienophile shows remarkable stability in water.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Total Synthesis of the Spirocyclic Imine Marine Toxin (−)-Gymnodimine and an Unnatural C4-Epimer
Ke Kong, Ziad Moussa, Changsuk Lee, and Daniel RomoJournal of the American Chemical Society2011 133 (49), 19844-19856Total Synthesis of the Spirocyclic Imine Marine Toxin (−)-Gymnodimine and an Unnatural C4-Epimer
Ke Kong, Ziad Moussa, Changsuk Lee, and Daniel RomoJournal of the American Chemical Society2011 133 (49), 19844-19856The first total synthesis of the marine toxin (−)-gymnodimine (1) has been accomplished in a convergent manner. A highly diastereo- and enantioselective exo-Diels–Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the ...
Effect of Counterion Structure on Rates and Diastereoselectivities in α,β-Unsaturated Iminium-Ion Diels–Alder Reactions
David Marcoux, Pascal Bindschädler, Alexander W. H. Speed, Anna Chiu, Joseph E. Pero, George A. Borg, and David A. EvansOrganic Letters2011 13 (14), 3758-3761Effect of Counterion Structure on Rates and Diastereoselectivities in α,β-Unsaturated Iminium-Ion Diels–Alder Reactions
David Marcoux, Pascal Bindschädler, Alexander W. H. Speed, Anna Chiu, Joseph E. Pero, George A. Borg, and David A. EvansOrganic Letters2011 13 (14), 3758-3761The use of cyclic α,β-unsaturated iminium-ion dienophiles is documented in two highly diastereoselective Diels–Alder (DA) reactions. The dienophilic counterion was found to have a significant effect on reactivity.
Total Synthesis of Sporolide B and 9-epi-Sporolide B
K. C. Nicolaou, Jianhua Wang, Yefeng Tang and Lorenzo BottaJournal of the American Chemical Society2010 132 (32), 11350-11363Total Synthesis of Sporolide B and 9-epi-Sporolide B
K. C. Nicolaou, Jianhua Wang, Yefeng Tang and Lorenzo BottaJournal of the American Chemical Society2010 132 (32), 11350-11363The total synthesis of the structurally unique secondary metabolite sporolide B (1b) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system ...
Studies Toward the Synthesis of Spirolides: Assembly of the Elaborated E-Ring Fragment
Craig E. Stivala and Armen ZakarianOrganic Letters2009 11 (4), 839-842Studies Toward the Synthesis of Spirolides: Assembly of the Elaborated E-Ring Fragment
Craig E. Stivala and Armen ZakarianOrganic Letters2009 11 (4), 839-842A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland−Claisen rearrangement. The E ring is completed by means of an ...
Studies toward a Marine Toxin Immunogen: Enantioselective Synthesis of the Spirocyclic Imine of (−)-Gymnodimine
Ke Kong, Ziad Moussa, and Daniel RomoOrganic Letters2005 7 (23), 5127-5130Studies toward a Marine Toxin Immunogen: Enantioselective Synthesis of the Spirocyclic Imine of (−)-Gymnodimine
Ke Kong, Ziad Moussa, and Daniel RomoOrganic Letters2005 7 (23), 5127-5130An enantioselective Diels−Alder reaction catalyzed by an Evans' copper−bis(oxazoline) complex was utilized to construct a highly functionalized spirolactam, a key intermediate in our projected total synthesis of the marine toxin, gymnodimine. Additional ...
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History
- Published In Issue September 01, 2005
- Received July 1, 2005
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