Chemoselective Nozaki–Hiyama–Takai–Kishi and Grignard reaction: short synthesis of some carbahexopyranoses

Vinaykumar, Allam; Surender, Banothu; Batchu, Venkateswara Rao

doi:10.1039/d3ra03704e

RSC Adv.

2023

DOI: 10.1039/d3ra03704e

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Chemoselective Nozaki–Hiyama–Takai–Kishi and Grignard reaction: short synthesis of some carbahexopyranoses

Allam Vinaykumar

Banothu Surender

Venkateswara Rao Batchu

Abstract: Stereoselective and short approach for synthesis of some carbahexopyranoses namely, MK7607, (−)-gabosine A, (−)-conduritol E, (−)-conduritol F, 6a-carba-β-d-fructopyranose and other carbasugars using chemoselective Grignard or NHTK reactions and RCM.

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Domino Reaction for the Synthesis of Substituted Pyrano[3′,4′:3,4]cyclopenta[1,2-c]chromenes Involving Double Ring Formation

Alizadeh,

Rostampoor

2024

J. Org. Chem.

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Herein, we present a green cascade approach for synthesizing a range of chemoselective polysubstituted pyrano-[3′,4′:3,4]cyclopenta[1,2-c]chromenes containing a chiral stereocenter. The strategy involves a metal-free nucleophilic reaction between dialkyl (2E)-2-{2-oxo-3-[(2E)-3-aryl-2-propenoyl]-2Hchromen-4-yl}-2-butenedioates and α,α-dicyanoolefins under reflux conditions in ethanol solvent. Mechanistic studies have shown that the reaction proceeds via a cascade of steps, including Michael addition, intramolecular C-and O-cyclization, intramolecular transesterification, [1,2]-H and [1,5]-methoxy-and ethoxy carbonyl shift, and finally aromatization to yield the desired product. In this method, three bonds (2C−C and C−O) form in one pot, simultaneously forming two new cyclopentane and pyrano rings by double cyclization reactions. Other advantages of this method are that it has a simple operation, readily available starting materials, a chemoselective cascade process, transition metal-free, synthetically useful yields, and green conditions by using ethanol as a solvent.

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Domino Reaction for the Synthesis of Substituted Pyrano[3′,4′:3,4]cyclopenta[1,2-c]chromenes Involving Double Ring Formation

Alizadeh,

Rostampoor

2024

J. Org. Chem.

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show abstract

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Chemoselective Nozaki–Hiyama–Takai–Kishi and Grignard reaction: short synthesis of some carbahexopyranoses

Abstract: Stereoselective and short approach for synthesis of some carbahexopyranoses namely, MK7607, (−)-gabosine A, (−)-conduritol E, (−)-conduritol F, 6a-carba-β-d-fructopyranose and other carbasugars using chemoselective Grignard or NHTK reactions and RCM.

Cited by 1 publication

References 76 publications

Domino Reaction for the Synthesis of Substituted Pyrano[3′,4′:3,4]cyclopenta[1,2-c]chromenes Involving Double Ring Formation

Domino Reaction for the Synthesis of Substituted Pyrano[3′,4′:3,4]cyclopenta[1,2-c]chromenes Involving Double Ring Formation

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