Stereoselective Synthesis of (E)- and (Z)-Acetals of Pent-2-en-4-yn-1-al and Related Dienynes and Dienediynes

Suzenet, Franck; Parrain, Jean‐Luc; Quintard, Jean‐Paul

doi:10.1002/(sici)1099-0690(199911)1999:11<2957::aid-ejoc2957>3.0.co;2-7

Cited by 7 publications

References 47 publications

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Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Garcia

Moulin

Miclo

et al. 2009

Chemistry A European J

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Three-ring circus: An expedient route to tricyclic fused 2-trimethylsilyl-3-aminopyridines exhibiting unprecedented skeletons is described. The key step is a very efficient cobalt-catalyzed [2+2+2] cycloaddition of a polyunsaturated compound displaying an ynamide, an alkyne, and a nitrile functionality (see picture). The first [2+2+2] cocyclizations between ynamides, nitriles, and alkynes are reported. They open a new access to unprecedented nitrogen-containing heterocycles of type 2-trimethylsilyl-3-aminopyridines. Such frameworks, which can be found in various compounds of biological interest, are very difficult to prepare by conventional methods. However, using [CpCo(C(2)H(4))(2)] (Cp=cyclopentadienyl) as catalyst, the intramolecular cyclizations could be achieved in up to 100 % yield. The presence of the trimethylsilyl group allowed a rare type of Hiyama cross-coupling: one of the silylated pyridines could be coupled with p-iodoanisole to give a new type of biaryl system.

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Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Garcia

Moulin

Miclo

et al. 2009

Chemistry A European J

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Callipeltosides A, B and C: Total Syntheses and Structural Confirmation

Frost

Pearson

Snaddon

et al. 2015

Chemistry A European J

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Since their isolation almost 20 years ago, the callipeltosides have been of long standing interest to the synthetic community owing to their unique structural features and inherent biological activity. Herein we present our full research effort that has led to the synthesis of these molecules. Key aspects of our final strategy include 1) synthesis of the C1–C9 pyran core (5) using an AuCl3-catalysed cyclisation; 2) formation of C10–C22 vinyl iodide (55) by sequential bidirectional Stille reactions and 3) diastereoselective union of these advanced fragments by means of an alkenylzinc addition (d.r.=91:9 at C9). The common callipeltoside aglycon (4) was completed in a further five steps. Following this, all three sugar fragments were appended to provide the entire callipeltoside family. In addition to this, D-configured callipeltose B was synthesised and appended to the callipeltoside aglycon. The 1H NMR spectrum of this molecule was found to be significantly different to the natural isolate, further supporting our assignment of callipeltoside B (2).

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ChemInform Abstract: Stereoselective Synthesis of (E)‐ and (Z)‐Acetals of Pent‐2‐en‐4‐yn‐1‐al and Related Dienynes and Dienediynes.

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Stereoselective Synthesis of (E)- and (Z)-Acetals of Pent-2-en-4-yn-1-al and Related Dienynes and Dienediynes

Cited by 7 publications

References 47 publications

Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Callipeltosides A, B and C: Total Syntheses and Structural Confirmation

ChemInform Abstract: Stereoselective Synthesis of (E)‐ and (Z)‐Acetals of Pent‐2‐en‐4‐yn‐1‐al and Related Dienynes and Dienediynes.

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Stereoselective Synthesis of (E)- and (Z)-Acetals of Pent-2-en-4-yn-1-al and Related Dienynes and Dienediynes

Cited by 7 publications

References 47 publications

Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular CoI‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular CoI‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Callipeltosides A, B and C: Total Syntheses and Structural Confirmation

ChemInform Abstract: Stereoselective Synthesis of (E)‐ and (Z)‐Acetals of Pent‐2‐en‐4‐yn‐1‐al and Related Dienynes and Dienediynes.

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Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes

Synthesis of Tricyclic Fused 3‐Aminopyridines through Intramolecular Co^I‐Catalyzed [2+2+2] Cycloaddition between Ynamides, Nitriles, and Alkynes