Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

Nobuyuki Hayashi; Masahisa Nakada

doi:10.1016/j.tetlet.2008.10.138

Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

Nobuyuki Hayashi, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

11 Citations (Scopus)

Abstract

The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.

Original language	English
Pages (from-to)	232-235
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.138
Publication status	Published - 2009 Jan 14

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.10.138

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title = "Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene",

abstract = "The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.",

author = "Nobuyuki Hayashi and Masahisa Nakada",

note = "Funding Information: We thank Dr. Nobuto Minowa (Meiji Seika Kaishya, Ltd, Japan) for kindly providing a sample of MK8383. This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research (B), and the Global COE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright} by MEXT. ",

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AU - Nakada, Masahisa

N1 - Funding Information: We thank Dr. Nobuto Minowa (Meiji Seika Kaishya, Ltd, Japan) for kindly providing a sample of MK8383. This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research (B), and the Global COE program ‘Center for Practical Chemical Wisdom’ by MEXT.

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AB - The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.

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Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

Abstract

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