A One-Step Synthesis of γ,δ-Unsaturated β-Ketoesters

Pollet, P.; Gelin, Suzanne

doi:10.1055/s-1978-24692

Cited by 34 publications

(9 citation statements)

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“…Fortunately, Nazarov-type ester 33 had already been described in the literature and provided a convenient starting point to launch an investigation into the synthesis of such dienes (Scheme ). Initially, ester 33 was synthesized by reaction of the dianion of ethyl hydrogen malonate, formed using a slight excess of isopropylmagnesium chloride, with methacryloyl chloride, followed by decarboxylation . However, upon scale-up of this route, the slightly lower yielding procedure of Miyata was employed, as this was more convenient and practical.…”

Section: Resultsmentioning

confidence: 99%

Two Approaches to the Aromatic Core of the Aminonaphthoquinone Antibiotics

et al. 2013

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Two complementary approaches are presented for the synthesis of the quinone chromophores of the naphthoquinone ansamycins and related natural products. The first involves the use of an improved protocol for the manganese(III) acetate mediated cyclization of 5-aryl-1,3-dicarbonyl compounds to β-naphthols, leading to the simple, scalable preparation of building blocks suitable for the synthesis of naturally occurring aminonaphthoquinones. The second approach involves the Diels-Alder reaction of a series of new, ester-containing Danishefsky-type dienes with N-protected aminobenzoquinones to allow more expeditious access to similar intermediates.

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Section: Resultsmentioning

confidence: 99%

Two Approaches to the Aromatic Core of the Aminonaphthoquinone Antibiotics

et al. 2013

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“…Finally, we will consider two strategies in which heterocyclic compounds act as synthetic equivalent In principle, the creation of this bond requires a carbanion attack of the center destined to become C4 at an electrophilic center that will become C3, following the electronic demand of a three-carbon atom fragment, progenitor of a /3-keto ester. Since C2 must not have H-atoms, the proposed methodologies concern exclusively a,a-disubstituted compounds, as exemplified by the chiral a-fluoro-a-methyl derivative (72), easily prepared by reaction of lithium dimethyl copper on the disubstituted ethyl malonyl chloride derivatives109 (Scheme 68). Scheme 66 Scheme 68 of /3-keto esters.…”

Section: E Miscellaneous Proceduresmentioning

confidence: 99%

Mastering .beta.-Keto Esters

Benetti¹,

Romagnoli²,

Risi³

et al. 1995

Chem. Rev.

247

136

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“…Since few examples of monoacylation were, however, known with acid chlorides, the reaction parameters were extensively reexamined. It was independently shown that, using two equivalents of isopropyl magnesium bromide (26)(27) or butyl lithium (28) as a base, a two-fold excess of ethyl hydrogen malonate was required to ensure a reproductive monoacylation and a high-yielding conversion of acid chlorides to 3ketoesters. Additional flexibility has been very recently given by the introduction of methyl and benzyl hydrogen malonates (29), thus allowing a similar preparation of methyl or benzyl 3-oxoalkynoates.…”

Section: -Acylation Of Ethyl Alkyl Mixed Malonates; An Improvementmentioning

confidence: 99%