Enantioselective construction of cis -hydroindole scaffolds via an asymmetric inverse-electron-demand Diels–Alder reaction: application to the formal total synthesis of (+)-minovincine

cis -Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis -hydroindoles is of great interest and importance. Herein, a novel approach for the en...

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Published inChemical science (Cambridge) Vol. 13; no. 19; pp. 5562 - 5567
Main Authors Zhang, Fangqing, Ren, Bing-Tao, Zhou, Yuqiao, Liu, Yangbin, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.05.2022
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Asymmetry
Chemistry
Chemistry, Multidisciplinary
Diels-Alder reactions
Enantiomers
Functional groups
Natural products
Physical Sciences
Scaffolds
Science & Technology
Stereoselectivity
VINCA ALKALOIDS
LIGANDS
NATURAL-PRODUCTS
CYCLOADDITIONS
CHEMISTRY
BIOMIMETIC ALKALOID SYNTHESES
OCTAHYDROINDOLES
COORDINATION
MATCHED 2-PYRONES
CYCLIZATION
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Abstract cis -Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis -hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis -hydroindole scaffolds has been realized through a chiral N , N ′-dioxide/Mg(OTf) 2 complex catalyzed asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis -hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
AbstractList cis-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis-hydroindole scaffolds has been realized through a chiral N,N′-dioxide/Mg(OTf)2 complex catalyzed asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
cis-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis-hydroindole scaffolds has been realized through a chiral N,N'-dioxide/Mg(OTf)2 complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.cis-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis-hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis-hydroindole scaffolds has been realized through a chiral N,N'-dioxide/Mg(OTf)2 complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
cis -Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis -hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis -hydroindole scaffolds has been realized through a chiral N , N ′-dioxide/Mg(OTf) 2 complex catalyzed asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis -hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
cis -Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of cis -hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of cis -hydroindole scaffolds has been realized through a chiral N , N ′-dioxide/Mg(OTf) 2 complex catalyzed asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted cis -hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method. An enantioselective IEDDA reaction between 2-pyrone and cyclic enamine was realized to construct cis -hydroindoles in high yield and ee, providing a concise route for formal total synthesis of (+)-minovincine.
-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and enantioselective methods for the construction of -hydroindoles is of great interest and importance. Herein, a novel approach for the enantioselective synthesis of -hydroindole scaffolds has been realized through a chiral , '-dioxide/Mg(OTf) complex catalyzed asymmetric inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones and cyclic enamines. A series of substituted -hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
Author Zhang, Fangqing
Liu, Yangbin
Feng, Xiaoming
Zhou, Yuqiao
Ren, Bing-Tao
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Keywords VINCA ALKALOIDS
LIGANDS
NATURAL-PRODUCTS
CYCLOADDITIONS
CHEMISTRY
BIOMIMETIC ALKALOID SYNTHESES
OCTAHYDROINDOLES
COORDINATION
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Snippet cis -Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient...
cis-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and...
-Hydroindole scaffolds widely exist in a large number of natural products, pharmaceuticals, and organocatalysts. Therefore, the development of efficient and...
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SubjectTerms Asymmetry
Chemistry
Chemistry, Multidisciplinary
Diels-Alder reactions
Enantiomers
Functional groups
Natural products
Physical Sciences
Scaffolds
Science & Technology
Stereoselectivity
Title Enantioselective construction of cis -hydroindole scaffolds via an asymmetric inverse-electron-demand Diels–Alder reaction: application to the formal total synthesis of (+)-minovincine
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Volume 13
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