Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Wu, Xiang; Wang, Haijun; Huang, Yong-Shuang; Li, Wei‐Dong Z.

doi:10.1021/acs.orglett.8b00407

Org. Lett.

2018

DOI: 10.1021/acs.orglett.8b00407

|View full text |Cite

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Xiang Wu

Haijun Wang

Yong-Shuang Huang

et al.

Abstract: Asymmetric total synthesis of (+)-sphaerodiol (2) has been achieved. A key step is an intramolecular [2 + 2] cycloaddition of alkyl(phenylthio)ketene for rapid assembly of the decalin ring.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2018

2024

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 8 publications

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes

Liu,

Lin,

Yoo

2024

Asian J Org Chem

View full text Add to dashboard Cite

An improved synthetic procedure for the intramolecular ketene [2+2] cycloaddition was developed for the preparation of 1‐heteroatom‐substituted bicyclo[2.1.1]hexan‐5‐ones. It was found that the use of the Mukaiyama reagent (2‐chloro‐N‐methyl‐pyridinium iodide) was key to efficiently generate the α‐heteroatom substituted homoallyl ketene intermediate for the cycloaddition reaction. The synthetic utility of the resulting bicyclic ketone was demonstrated through the preparation of a bioisosteric variant of vortioxetine.

show abstract

Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes

Liu,

Lin,

Yoo

2024

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Anellierte Cyclobutane durch Fe‐katalysierte Cycloisomerisierung von Eninacetaten

et al. 2018

View full text Add to dashboard Cite

show abstract

Annelated Cyclobutanes by Fe‐Catalyzed Cycloisomerization of Enyne Acetates

et al. 2018

View full text Add to dashboard Cite

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

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

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.

Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol

Abstract: Asymmetric total synthesis of (+)-sphaerodiol (2) has been achieved. A key step is an intramolecular [2 + 2] cycloaddition of alkyl(phenylthio)ketene for rapid assembly of the decalin ring.

Cited by 8 publications

References 74 publications

Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes

Intramolecular [2+2] Cycloadditions of α‐Heteroatom Substituted γ,δ‐Unsaturated Ketenes

Anellierte Cyclobutane durch Fe‐katalysierte Cycloisomerisierung von Eninacetaten

Annelated Cyclobutanes by Fe‐Catalyzed Cycloisomerization of Enyne Acetates

Contact Info

Product

Resources

About