Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

Tomohiro Fujii; Masahisa Nakada

doi:10.1016/j.tetlet.2014.01.071

Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

Tomohiro Fujii, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

8 Citations (Scopus)

Abstract

A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.

Original language	English
Pages (from-to)	1597-1601
Number of pages	5
Journal	Tetrahedron Letters
Volume	55
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2014.01.071
Publication status	Published - 2014 Feb 26

Keywords

Fusidane
Intermolecular
Michael reaction
Stereoselective
Transannular

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.01.071

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title = "Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade",

abstract = "A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.",

keywords = "Fusidane, Intermolecular, Michael reaction, Stereoselective, Transannular",

author = "Tomohiro Fujii and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by the Waseda University Grant for Special Research Projects, The Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Organic Synthesis based on Reaction Integration, Development of New Methods and Creation of New Substances{\textquoteright} (No. 2105), and Grants for Excellent Graduate Schools (Practical Chemical Wisdom), MEXT, Japan. ",

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doi = "10.1016/j.tetlet.2014.01.071",

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AU - Fujii, Tomohiro

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by the Waseda University Grant for Special Research Projects, The Grant-in-Aid for Scientific Research on Innovative Areas ‘Organic Synthesis based on Reaction Integration, Development of New Methods and Creation of New Substances’ (No. 2105), and Grants for Excellent Graduate Schools (Practical Chemical Wisdom), MEXT, Japan.

PY - 2014/2/26

Y1 - 2014/2/26

N2 - A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.

AB - A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships.

KW - Fusidane

KW - Intermolecular

KW - Michael reaction

KW - Stereoselective

KW - Transannular

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Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

Abstract

Keywords

ASJC Scopus subject areas

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