An efficient synthesis of magallanesine using [1,2]-Meisenheimer rearrangement and Heck cyclization

Yoneda, R.; Sakamoto, Y.; Oketo, Y.; Harusawa, Shinya; Kurihara, Takushi

doi:10.1016/0040-4020(96)00900-3

Cited by 38 publications

(14 citation statements)

References 31 publications

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“…Azetidine N-oxides are usually unstable at room temperature, undergoing a [1,2] rearrangement. 1 Only one example of an azetidine N-oxide stable at room temperature has been reported. 2 In this case the azetidine ring was fused to a six membered ring.…”

mentioning

confidence: 99%

Simple azetidine N-oxides: synthesis, structure and reactivity

O’Neil¹,

Potter²

1998

Chem. Commun.

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mentioning

confidence: 99%

Simple azetidine N-oxides: synthesis, structure and reactivity

O’Neil¹,

Potter²

1998

Chem. Commun.

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“…Ring Expansions of Nonactivated Aziridines and Azetidines same group, en route to Magallanesine [114]: in this report, the unstable azetidine N-oxide obtained by oxidation of 219 undergoes a regioselective Meisenheimer rearrangement yielding isoxazolidine 220, a precursor to the eight-membered ring of Magallanesine 221 (Scheme 58).…”

Section: Expansions Into Isoxazolidinesmentioning

confidence: 93%

Ring Expansions of Nonactivated Aziridines and Azetidines

Couty

David

2015

Topics in Heterocyclic Chemistry

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Ring expansions promoted by ring strain in aziridines and azetidines are reviewed in this chapter, putting emphasis on recent applications from the last decade. This vast subject cannot be surveyed here exhaustively, and the reader will be guided to relevant precedent reviews or key reports. Rather, special attention will be put on selected examples and their mechanistic details, aiming to demonstrate that high selectivity can be reached in these reactions. In this issue, this fastgrowing topic has been divided into two distinct chapters, this one dealing with "nonactivated" aziridines and azetidines. Therefore, the reader will only find here examples involving NH-or N-alkylaziridines and N-azetidines as substrates for ring expansions, while N-acyl, N-carbamoyl, or N-tosyl compounds, defined as "activated" substrates, will be presented in the next chapter. This distinction can appear quite arbitrary at first sight but is amply justified by the great difference in reactivity of these distinct substrates. The first part focuses on the ring expansions of nonactivated aziridines into up to seven-membered rings and is further divided into expansions involving the incorporation of one (or more) heteroatoms, followed by ring expansions involving only incorporation of carbon atoms. The same model is then followed for azetidines.

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“…In 1996, Kurihara (Scheme 13) reported a [1,2]-Meisenheimer rearrangement followed by an intramolecular Heck cyclization to elaborate the isoindolobenzazocine moiety [85]. The synthesis commenced with the preparation of ester 106 from piperonal according to a known procedure [86].…”

Section: Reviewmentioning

confidence: 99%

“…Amide formation with acid chloride 110 gave 111 , which upon sequential oxidation yielded enaminone 112 . Finally, the isoindolinone moiety was generated via an intramolecular Heck reaction using tetrakis(triphenylphosphine)palladium(0) and thallium acetate, to give magallanesine ( 97 ) in excellent yield [85]. …”

Section: Reviewmentioning

confidence: 99%

The chemistry of isoindole natural products

Speck¹,

Magauer²

2013

Beilstein J. Org. Chem.

316

163

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SummaryThis review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

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An efficient synthesis of magallanesine using [1,2]-Meisenheimer rearrangement and Heck cyclization

Cited by 38 publications

References 31 publications

Simple azetidine N-oxides: synthesis, structure and reactivity

Simple azetidine N-oxides: synthesis, structure and reactivity

Ring Expansions of Nonactivated Aziridines and Azetidines

The chemistry of isoindole natural products

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