Synthesis of Proteasome Inhibitor Omuralide Featuring Stereocontrolled Ugi Reaction and Novel Convertible Isocyanide

Gilley, Cynthia B.; Buller, Matthew J.; Kobayashi, Yohnosuke

doi:10.5059/yukigoseikyokaishi.67.1183

Cited by 4 publications

(2 citation statements)

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“…[59][60][61] The Ugi-4CR afforded predominantly anti-48 in good yield, but with only moderate diastereoselectivity (Scheme 16). [59][60][61] The Ugi-4CR afforded predominantly anti-48 in good yield, but with only moderate diastereoselectivity (Scheme 16).…”

Section: Diastereoselective Ugi Reactionsmentioning

confidence: 99%

“…In 2008, Kobayashi and co-workers described the diastereoselective outcome of an Ugi four-center (4C) threecomponent reaction (Ugi-4C-3CR) involving a β-hydroxy γ-keto acid, which was subsequently used in a formal total synthesis of the proteasome inhibitor omuralide. [59][60][61] The Ugi-4CR afforded predominantly anti-48 in good yield, but with only moderate diastereoselectivity (Scheme 16). The low diastereoselectivity might be a result of the unprotected alcohol, so protection might induce higher stereoselectivity.…”

Section: Diastereoselective Ugi Reactionsmentioning

confidence: 99%

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Recent Advances in Asymmetric Isocyanide‐Based Multicomponent Reactions

et al. 2012

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Section: Diastereoselective Ugi Reactionsmentioning

confidence: 99%

Section: Diastereoselective Ugi Reactionsmentioning

confidence: 99%

Recent Advances in Asymmetric Isocyanide‐Based Multicomponent Reactions

et al. 2012

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A Half‐Century of the Ugi Reaction: Modified Variants

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process involving a carboxylic acid, a carbonyl compound, an amine, and an isocyanide, resulting in an N ‐acylamino acid amide product. Modified Ugi reactions employ special, often multifunctional, reaction components, and can involve fewer than or more than four components. This reaction exhibits broad scope and can be used to prepare complex heterocycles. As a result, this method has been employed to prepare diverse libraries of structurally related products, and in addition, is often applied to the synthesis of drugs, drug‐like molecules, and natural products. Applications in target‐directed synthesis are presented, as are comparisons to other related multicomponent reactions and heterocycle syntheses; modifications leading to achiral heteroaromatic ring systems are not included. This chapter covers the literature from the early days of the Ugi reaction in 1961 through the end of 2012.

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