Estafiatin, a new sesquiterpene lactone isolated from Artemisia mexicana (Willd)

Sánchez‐Viesca, Francisco; Romo, J.

doi:10.1016/s0040-4020(01)98591-6

Cited by 77 publications

(28 citation statements)

References 14 publications

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“…The stereoselective synthesis of the natural product (-)-estafiatin (96), a sesquiterpene lactone isolated from Artemisia mexicana [155], was developed by Rabi et al [154,156]. The sequences of reactions used for the synthesis of this natural product are depicted in Schemes 22-23.…”

Section: Synthesis Of (-)-Estafiatinmentioning

confidence: 99%

“…The bromohydrin 123 was prepared by reaction of dibromoether 2 with zinc in refluxing MeOH. [168,169] H 2 (5 psi)/5% PdS-C EtOH (r. t., 1.5 h) (100%) [150] NaOH-H 2 O DMF (reflux, 2.5 h) (85%) [168,169] NaOH-H2O DMF (reflux, 3 h) (80%) [168,169] Scheme 38: Syntheses of micheliolide (155) and 1R, 10R-dihydromicheliolide (154).…”

Section: Study Of 13 C Nmr Spectroscopy On Eremanthine Derivativesmentioning

confidence: 99%

“…Study on the Synthesis of Micheliolide. The synthesis of micheliolide (155) was studied by the sequences of reactions depicted in Schemes 37 and 38. Initial attempts to deoxygenate the C-9 position of acetate 148 and iodohydrin 139 with concomitant hydrogenolysis of the bond C15-I in these compounds were unsuccessful [150].…”

Section: Study Of the Inversion Reaction Of The Lactonic Fusion On Ermentioning

confidence: 99%

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A Review on the Chemistry of Eremanthine: A Sesquiterpene Lactone with Relevant Biological Activity

Alves

2011

Organic Chemistry International

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Section: Synthesis Of (-)-Estafiatinmentioning

confidence: 99%

Section: Study Of 13 C Nmr Spectroscopy On Eremanthine Derivativesmentioning

confidence: 99%

Section: Study Of the Inversion Reaction Of The Lactonic Fusion On Ermentioning

confidence: 99%

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A Review on the Chemistry of Eremanthine: A Sesquiterpene Lactone with Relevant Biological Activity

Alves

2011

Organic Chemistry International

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“…[21] Furthermore, variation of this route allowed the synthesis of (Ϯ)-estafiatin (4), [19a,19c] a natural product first isolated by Romo and coworkers from Artemisia mexicana. [22] The opening step entails the epoxidation of the double bond in the five-membered ring of (Ϯ)-44. Controlled by steric hindrance (shielding of the β-face by the encumbering ketal protecting group), the bulkiest reagent gave the best selectivity of 6:1 for α-epoxide (Ϯ)-50 (Scheme 9, top), providing the correct stereochemistry needed for the subsequent transformation into (Ϯ)-compressanolide (5).…”

Section: Total Synthesis Of (؎)-Compressanolide and (؎)-Estafiatinmentioning

confidence: 99%

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Schall

Reiser

2008

Eur J Org Chem

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The biosynthetic pathways of sesquiterpene lactones are described in conjunction with recent developments in the total syntheses of various biologically active guaianolides. Different strategies towards the 5,7,5‐membered ring system are highlighted. Oxidative diol cleavages, aldol reactions, and intramolecular cyclopropanations were used as key reactions to construct the racemic guaianolide core system. Radical cyclizations, as well as ring closing metathesis, were successfully applied in asymmetric approaches. Biomimetic reactions were also applied as versatile tools for the construction of these highly complex natural products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…The NMR spectrum of tetrahydroestafiatin (10) 19 shows for the C-3 epoxiproton a singlet at 3.29 pprn with a line width of 3.0 Hz. Upon irradiation of the C-4 methyl frequency at 1.54 ppm, the C-3 proton signal height observing an interaction involving coupling and not a case of the well known nuclear Overhauser effect.…”

mentioning

confidence: 99%

Long‐range proton‐proton interactions through epoxides

Joseph‐Nathan

Dı́az

1971

Org. Magn. Reson.

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Double and triple nuclear magnetic resonance experiments performed at 100 MHz demonstrate the existence of long range 'H--'H couplings through epoxides. In a series of epoxycontaining sesquiterpenoids, interactions between protons separated by up to six sigma bonds were detected. These interactions may have origins similar to the well-known allylic and homoallylic couplings found in carbon-carbon double bonded compounds, although they are much smaller in the epoxy systems. We propose to name them as 'epoallylic' and 'epohomoallylic' interactions. Some couplings are observed directly, whereas in other cases only an improvement in resolution is seen during multiple irradiation experiments. Even in these latter cases the areas of the observed peak do not change upon multiple irradiation which demonstrates the absence of nuclear Overhauser effects. The stereochemistry of some asymmetric centers of the compounds studied is deduced from the spectra.

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Estafiatin, a new sesquiterpene lactone isolated from Artemisia mexicana (Willd)

Cited by 77 publications

References 14 publications

A Review on the Chemistry of Eremanthine: A Sesquiterpene Lactone with Relevant Biological Activity

A Review on the Chemistry of Eremanthine: A Sesquiterpene Lactone with Relevant Biological Activity

Synthesis of Biologically Active Guaianolides with a trans‐Annulated Lactone Moiety

Long‐range proton‐proton interactions through epoxides

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