ChemInform Abstract: Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin.

Poral, Vincent L; Furkert, Daniel P.; Brimble, Margaret A.

doi:10.1002/chin.201619183

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2019

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“…[18][19][20][21][22][23] Recently, an enantioselective total synthesis of lasionectrin has also been reported. 24 Herein, we report a short and practical synthesis of monocerin and its acetate derivative in optically active form. The synthesis features a Sharpless asymmetric dihydroxylation, a Lewis-acid catalyzed oxocarbenium ion-mediated stereoselective allylation, a formulation reaction, and a CrO 3 mediated oxidation of the benzopyran to a dihydroisocoumarin derivative.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

Ghosh

Lee

2019

J. Org. Chem.

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We describe here the enantioselective synthesis of (+)-monocerin and its acetate derivative. The present synthesis features an efficient optically active synthesis of the β-hydroxy-γ-lactone derivative with high enantiomeric purity using a Sharpless dihydroxylation as the key step. The synthesis also highlights a tandem Lewis acid-catalyzed, oxocarbenium ion-mediated diastereoselective syn-allylation reaction and a methoxymethyl group promoted methylenation reaction. A selective CrO 3-mediated oxidation of isochroman provided the corresponding lactone derivative. We investigated this reaction with a variety of Lewis acids. The synthesis is quite efficient and may be useful for the preparation of derivatives.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

Ghosh

Lee

2019

J. Org. Chem.

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ChemInform Abstract: Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin.

Abstract: The total synthesis of lasionectrin (I) shows that the natural product is the enantiomer of the initially proposed structure.

Cited by 1 publication

References 1 publication

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

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