Enantioselective total synthesis of (+)-digitoxigenin

Masahiro Honma; Masahisa Nakada

doi:10.1016/j.tetlet.2007.01.024

Enantioselective total synthesis of (+)-digitoxigenin

Masahiro Honma, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

51 Citations (Scopus)

Abstract

An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

Original language	English
Pages (from-to)	1541-1544
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2007.01.024
Publication status	Published - 2007 Feb 26

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.01.024

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title = "Enantioselective total synthesis of (+)-digitoxigenin",

abstract = "An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.",

author = "Masahiro Honma and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from The Ministry of Education, Culture, Sports, Science, and Technology, Japan. We are also indebted to 21COE {\textquoteleft}Practical Nano-Chemistry{\textquoteright}. The fellowship for young scientists to M.H. from JSPS is also gratefully acknowledged.",

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T1 - Enantioselective total synthesis of (+)-digitoxigenin

AU - Honma, Masahiro

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects and a Grant-in-Aid for Scientific Research on Priority Areas (Creation of Biologically Functional Molecules (No. 17035082)) from The Ministry of Education, Culture, Sports, Science, and Technology, Japan. We are also indebted to 21COE ‘Practical Nano-Chemistry’. The fellowship for young scientists to M.H. from JSPS is also gratefully acknowledged.

PY - 2007/2/26

Y1 - 2007/2/26

N2 - An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

AB - An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.

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DO - 10.1016/j.tetlet.2007.01.024

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Enantioselective total synthesis of (+)-digitoxigenin

Abstract

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