Biomimetic synthesis of the bisindole framework present in sciodole, an alkaloid from<i>Tricholoma sciodes</i>

Homer, Joshua A.; Sperry, Jonathan

doi:10.1039/c8ob02142b

Org. Biomol. Chem.

2018

DOI: 10.1039/c8ob02142b

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Biomimetic synthesis of the bisindole framework present in sciodole, an alkaloid fromTricholoma sciodes

Joshua A. Homer

Jonathan Sperry

Abstract: A synthesis of the unique bisindole framework present in the mushroom-derived alkaloid sciodole has been achieved, validating a biosynthesis proposal that the C-N bisindole bond present in the natural product is forged by amination of an azafulvenium.

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Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1H-pyrrolizines

Kallweit

Schneider

2019

Org. Lett.

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We describe herein an organocatalytic, diastereo-and enantioselective [6 + 2]-cycloaddition toward the synthesis of densely substituted 2,3-dihydro-1H-pyrrolizines bearing three contiguous stereogenic centers which are obtained with good yields, as single diastereomers, and with excellent enantioselectivity. A crucial feature of this one-step process leading to a prominent structural motif in many biologically active natural products is a BINOL-derived phosphoric acid catalyzed reaction of 1H-pyrrole-2-yl carbinols with 2-vinylindoles via the corresponding hydrogen-bonded chiral 2-methide-2H-pyrroles.

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Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1H-pyrrolizines

Kallweit

Schneider

2019

Org. Lett.

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Biomimetic synthesis of the bisindole framework present in sciodole, an alkaloid fromTricholoma sciodes

Abstract: A synthesis of the unique bisindole framework present in the mushroom-derived alkaloid sciodole has been achieved, validating a biosynthesis proposal that the C-N bisindole bond present in the natural product is forged by amination of an azafulvenium.

Cited by 1 publication

References 39 publications

Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1H-pyrrolizines

Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1H-pyrrolizines

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