3‐Functionalized Tetronic Acids From Domino Rearrangement/Cyclization/Ring‐Opening Reactions of Allyl Tetronates

Schobert, Rainer; Gordon, G. J.; Bieser, Arno M.; Milius, Wolfgang

doi:10.1002/ejoc.200300283

Cited by 16 publications

(9 citation statements)

References 18 publications

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“…White solid (194 mg, 60%), R f 0. 25 3.6. Melophlin C-typical procedure for the synthesis of melophlins 1 from tetramates 9…”

Section: Synthesis Of Methyldodecanoyl Chlorides (G)-7mentioning

confidence: 99%

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An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

Schobert

Jagusch

2005

Tetrahedron

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“…White solid (194 mg, 60%), R f 0. 25 3.6. Melophlin C-typical procedure for the synthesis of melophlins 1 from tetramates 9…”

Section: Synthesis Of Methyldodecanoyl Chlorides (G)-7mentioning

confidence: 99%

“…This parallels the conversion of a-hydroxyesters to the corresponding tetronates, developed and exploited by us previously. [24][25][26] Procedural advantages of using immobilized, resin-bound Ph 3 PCCO are discussed.…”

Section: Introductionmentioning

confidence: 99%

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

Schobert

Jagusch

2005

Tetrahedron

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“…74 Yates et al demonstrated that even one activating EWG in spirocyclopropanes 37a-e facilitated their ring opening by morpholine yielding cyclohexanone derivatives 38a-c (Scheme 15). 75 Notably, an exocyclic double bond significantly increased the reactivity of cyclopropanes 37a,b in comparison with cyclopropanes 37c,d, containing an endocyclic double bond, and their saturated counterpart 37e.…”

Section: Scheme 12mentioning

confidence: 99%

“…153 The efficiency of this reagent was demonstrated in the ring opening of ketocyclopropane 19а, Schobert et al 74 found that spiro-activated DA cyclopropanes 35 react with nitriles in a reaction catalyzed by ytterbium(III) triflate, a Lewis acid of average strength (Scheme 103). …”

Section: Ring Opening With Pyrimidinesmentioning

confidence: 99%

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

et al. 2017

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Ring opening of donor-acceptor cyclopropanes with variousN-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor-acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

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“…Due to ring strain and the electron withdrawing influence of the two adjacent carbonyl groups, the cyclopropane ring in the spiro compounds is amenable to opening by attack of nucleophiles. It is of interest that this is a regio-and stereoselective process (Schobert et al 2003a). For example, as shown in Fig.…”

Section: Tetronic Acids From Extended Domino Sequencesmentioning

confidence: 99%

Domino syntheses of bioactive tetronic and tetramic acids

Schobert

2006

Naturwissenschaften

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Natural products containing tetronic acid or tetramic acid moieties continue to attract the interest of chemists, biologists, and physicians due to their challenging structures and to the wide range of biological activities they display. This review portrays the structural varieties of tetronic and tetramic acids and the spectrum of possible therapeutically relevant effects in man for exemplary derivatives. Their biosynthetic origin from alpha-amino and alpha-hydroxy acids is briefly discussed as is the relationship between their structures and their modes of interaction with biochemical effectors such as metal cations or enzymes. A short overview of laboratory syntheses of the heterocyclic core structures of tetramic and tetronic acids is provided with an emphasis on those emulating the biosynthesis. A synthesis from the alpha-amino or alpha-hydroxy esters and the cumulated phosphorus ylide Ph(3)PCCO based upon a domino addition-intra-Wittig alkenation sequence is presented with applications to the preparation of the antibiotics reutericyclin and tenuazonic acid, the cytotoxic melophlin B, and the enzyme inhibitor RK-682. Procedural advantages of immobilizing either starting component by attaching it to a resin and its exploitation in the parallel synthesis of libraries of potential drug candidates are described. The basic domino reaction can even be extended by further C-C bond forming steps when starting from suitable alpha-hydroxy or alpha-amino allyl esters. Depending on the chosen reaction conditions, bioactive intermediates of formally three to seven step long cascades can be obtained. Among them, herbicidal 3-alkyltetronic acids and lactone endoperoxides with antiplasmodial activity exceeding that of the natural antimalarial lead artemisinin. Hence, this domino reaction gives access to diversely functionalized derivatives of tetronic and tetramic acids. As it can also be ported to solid phase, it is ideally suited for parallel and combinatorial processing. Future developments might include running such domino sequences in continuous mode in arrays of "labs on microchips".

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3‐Functionalized Tetronic Acids From Domino Rearrangement/Cyclization/Ring‐Opening Reactions of Allyl Tetronates

Cited by 16 publications

References 18 publications

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

Domino syntheses of bioactive tetronic and tetramic acids

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3‐Functionalized Tetronic Acids From Domino Rearrangement/Cyclization/Ring‐Opening Reactions of Allyl Tetronates

Cited by 16 publications

References 18 publications

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Domino syntheses of bioactive tetronic and tetramic acids

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Product

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Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles