Recent development of vinylogous Mukaiyama aldol reactions

Seijiro Hosokawa

doi:10.1016/j.tetlet.2017.11.056

Recent development of vinylogous Mukaiyama aldol reactions

Seijiro Hosokawa

School of Advanced Science and Engineering

Research output: Contribution to journal › Review article › peer-review

33 Citations (Scopus)

Abstract

The vinylogous Mukaiyama aldol reaction (VMAR) is a powerful tool of polyketide synthesis, which constructs a large size structure by simultaneous introduction of the stereogenic center(s) and the α,β-unsaturated carbonyl group. A variety of stereocontrolled VMARs have been developed and applied to natural product synthesis. This review is focused on recent development of the vinylogous Mukaiyama aldol reaction using s-trans silyl dienolates.

Original language	English
Pages (from-to)	77-88
Number of pages	12
Journal	Tetrahedron Letters
Volume	59
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2017.11.056
Publication status	Published - 2018 Jan 10

Keywords

Natural product synthesis
Polyketide
Silyl dienolate
Stereoselective synthesis
Vinylogous Mukaiyama aldol reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.11.056

Cite this

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title = "Recent development of vinylogous Mukaiyama aldol reactions",

abstract = "The vinylogous Mukaiyama aldol reaction (VMAR) is a powerful tool of polyketide synthesis, which constructs a large size structure by simultaneous introduction of the stereogenic center(s) and the α,β-unsaturated carbonyl group. A variety of stereocontrolled VMARs have been developed and applied to natural product synthesis. This review is focused on recent development of the vinylogous Mukaiyama aldol reaction using s-trans silyl dienolates.",

keywords = "Natural product synthesis, Polyketide, Silyl dienolate, Stereoselective synthesis, Vinylogous Mukaiyama aldol reaction",

author = "Seijiro Hosokawa",

note = "Funding Information: Authors are grateful for financial support to The NOVARTIS Foundation (Japan) for the Promotion of Science, The Kurata Memorial Hitachi Science and Technology Foundation, The Naito Foundation, The Sumitomo Foundation, and MEXT, Japan. Funding Information: Authors are grateful for financial support to The NOVARTIS Foundation (Japan) for the Promotion of Science, The Kurata Memorial Hitachi Science and Technology Foundation , The Naito Foundation , The Sumitomo Foundation , and MEXT , Japan. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

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N2 - The vinylogous Mukaiyama aldol reaction (VMAR) is a powerful tool of polyketide synthesis, which constructs a large size structure by simultaneous introduction of the stereogenic center(s) and the α,β-unsaturated carbonyl group. A variety of stereocontrolled VMARs have been developed and applied to natural product synthesis. This review is focused on recent development of the vinylogous Mukaiyama aldol reaction using s-trans silyl dienolates.

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KW - Silyl dienolate

KW - Stereoselective synthesis

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Recent development of vinylogous Mukaiyama aldol reactions

Abstract

Keywords

ASJC Scopus subject areas

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