Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

Daniel Zárate-Zárate; Raúl Aguilar; R. Israel Hernández-Benitez; Ehecatl M. Labarrios; Francisco Delgado; Joaquín Tamariz

doi:10.1016/j.tet.2015.07.010

Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

Daniel Zárate-Zárate, Raúl Aguilar, R. Israel Hernández-Benitez, Ehecatl M. Labarrios, Francisco Delgado, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized α-ketols, including natural alkaloid actinopolymorphol B (24a). The α-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives.

Original language	English
Pages (from-to)	6961-6978
Number of pages	18
Journal	Tetrahedron
Volume	71
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2015.07.010
State	Published - 12 Aug 2015

Keywords

1-Acetylvinyl p-nitrobenzoyloxy
4-Oxazolin-2-ones
Actinopolymorphol B
Captodative alkenes
Tanakine
α-Ketols

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10.1016/j.tet.2015.07.010

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title = "Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products",

abstract = "Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized α-ketols, including natural alkaloid actinopolymorphol B (24a). The α-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives.",

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author = "Daniel Z{\'a}rate-Z{\'a}rate and Ra{\'u}l Aguilar and Hern{\'a}ndez-Benitez, {R. Israel} and Labarrios, {Ehecatl M.} and Francisco Delgado and Joaqu{\'i}n Tamariz",

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doi = "10.1016/j.tet.2015.07.010",

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T1 - Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

AU - Zárate-Zárate, Daniel

AU - Aguilar, Raúl

AU - Hernández-Benitez, R. Israel

AU - Labarrios, Ehecatl M.

AU - Delgado, Francisco

AU - Tamariz, Joaquín

PY - 2015/8/12

Y1 - 2015/8/12

N2 - Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized α-ketols, including natural alkaloid actinopolymorphol B (24a). The α-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives.

AB - Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized α-ketols, including natural alkaloid actinopolymorphol B (24a). The α-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives.

KW - 1-Acetylvinyl p-nitrobenzoyloxy

KW - 4-Oxazolin-2-ones

KW - Actinopolymorphol B

KW - Captodative alkenes

KW - Tanakine

KW - α-Ketols

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U2 - 10.1016/j.tet.2015.07.010

DO - 10.1016/j.tet.2015.07.010

M3 - Artículo

SN - 0040-4020

VL - 71

SP - 6961

EP - 6978

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

Abstract

Keywords

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