Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

Burns, Alan R.; Taylor, Richard J.K.

doi:10.1055/s-0030-1258335

Synthesis

2010

DOI: 10.1055/s-0030-1258335

|View full text |Cite

Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

Alan R. Burns¹,

Richard J.K. Taylor²

Abstract: 4-Hydroxycyclohex-2-en-1-one and its derivatives have been used as the key chiral building blocks in a number of natural product and complex molecule syntheses. This review describes the many and varied methods for preparing the title compound in an enantioselective manner and also details how it has been utilised in natural product synthesis.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2016

2022

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Chiral Brønsted Acid-Catalyzed Asymmetric Allyl(propargyl)boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity

et al. 2016

View full text Add to dashboard Cite

Chiral Brønsted acid-catalyzed allyl(propargyl)boration of ortho-alkynyl benzaldehydes gives rise to ω-alkynyl homoallylic(homopropargylic)alcohols that can be further transformed to complex molecular scaffolds via subsequent hydroalkoxylation, ring-closing enyne metathesis (RCEYM), or intramolecular Pauson−Khand reaction (PKR). Optimizations of each two-step transformation is reported. A strong dependence between enantioselectivities and the nature of the substitution at the alkynyl moiety is observed, showcasing that the triple bond is not merely a spectator in this transformation. Density functional theory (DFT) calculations (M06-2X/6-311+G(d,p)−IEFPCM//B3LYP/6-31G(d)) show that this dependence is the result of the steric and electronic properties of the alkyne substituent.

show abstract

Chiral Brønsted Acid-Catalyzed Asymmetric Allyl(propargyl)boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity

et al. 2016

View full text Add to dashboard Cite

show abstract

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Jurado

Domı́nguez-Pérez

Illa

et al. 2022

IJMS

View full text Add to dashboard Cite

The enantioselective preparation of the two isomers of 4-hydroxy-2-cyclohexanone derivatives 1a,b was achieved, starting from a common cyclohexenone, through asymmetric transfer hydrogenation (ATH) reactions using bifunctional ruthenium catalysts. From these versatile intermediates, a stereoselective route to a cytosine analogue built on a bicyclo [4.1.0]heptane scaffold is described. Nucleoside kinase activity assays with this cyclopropyl-fused cyclohexane nucleoside, together with other related nucleosides (2a–e), were performed, showing that thymine- and guanine- containing compounds have affinity for herpes simplex virus Type 1 (HSV-1) thymidine kinase (TK) but not for human cytosolic TK-1, thus pointing to their selectivity for herpetic TKs but not cellular TKs.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

Cited by 2 publications

References 65 publications

Chiral Brønsted Acid-Catalyzed Asymmetric Allyl(propargyl)boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity

Chiral Brønsted Acid-Catalyzed Asymmetric Allyl(propargyl)boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity

Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Contact Info

Product

Resources

About