Stereoselective carbocyclization of hanphyllin with N-bromosuccinimide

Merkhatuly, N.; Zhokizhanova, S. K.; Balmagambetova, L. T.; Адекенов, С. М.

doi:10.1134/s1070363206080378

Russ J Gen Chem

2006

DOI: 10.1134/s1070363206080378

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Stereoselective carbocyclization of hanphyllin with N-bromosuccinimide

N. Merkhatuly

S. K. Zhokizhanova

L. T. Balmagambetova

et al.

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“…In extension of our research in the field of biomimetic transformations of germacranic sesquiterpene γ-lactones [1,2] we performed by the action of formic acid a stereocontrolled transannular carbocyclization of Е,Е-germanocranolide hanphillin (I) isolated from Noble Yarrow (Achillea nobilis L.), and obtained new trans-fused 5α(Н),10β(СH 3 )eudesmanolides II and III in the yields of 65 and 30% respectively.…”

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Stereocontrolled acid cyclization of (+)-hanphillin

et al. 2014

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In extension of our research in the field of biomimetic transformations of germacranic sesquiterpene γ-lactones [1, 2] we performed by the action of formic acid a stereocontrolled transannular carbocyclization of Е,Е-germanocranolide hanphillin (I) isolated from Noble Yarrow (Achillea nobilis L.), and obtained new trans-fused 5α(Н),10β(СH 3 )eudesmanolides II and III in the yields of 65 and 30% respectively.As shown in the scheme the acid-catalyzed 5,10carbocyclization of compound I proceeds evidently through a regioselective protonation of the most electron-donor and spatially available Δ 1,10 -double bond of compound I followed by a stereospecific nucleophilic attack by the Δ 4,5 -double bond leading via a tertiary carbocation to the trans-fused eudesmanolides II and III (Scheme 1).The stereocontrolled 5,10-carbocyclization of compound I occurs also in the presence of СН 3 СО 3 Н and С 6 Н 5 СО 3 Н in СH 2 Сl 2 at room temperature giving trans-eudesmanolides formerly isolated from plant sources [3, 4] epiartekalin (IV) and ridentin-В (V) in 45 and 53% yields (Scheme 2).Compounds II and III. To a solution of 0.3 g (1.2 mmol) of compound I in 15 mL of СНСl 3 was added dropwise at room temperature 4.6 mL of 99% НСО 2 Н. The reaction mixture was stirred at room temperature, then washed with 10% solution of NaHCO 3 (2 × 10 mL), with water (3 × 10 mL), dried with MgSO 4 , the solvent was distilled off in a vacuum. The residue (0.33 g) was chromatographed on a column packed with silica gel (eluent hexane-ethyl acetate, 2 : 3 and 1 : 4). -1 1 (1 3)-e n -6, 12 -ol i d e , o r (3aS,5aS,9R,9aS,9bS)-5a,9-dimethyl-3-methylideneoctahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione (II). Yield 0.193 g (65%). R f 0.54 (hexane-ethyl acetate, 2 : 3). Colorless crystals, mp 136-138°С. -O xo e u d es m

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Stereocontrolled acid cyclization of (+)-hanphillin

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Ti-catalyzed transannular cyclization of epoxygermacrolides. Synthesis of antifungal (+)-tuberiferine and (+)-dehydrobrachylaenolide

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Biomimetic cyclization of Е,Е-germacranolide (+)-hanphilline

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Stereoselective carbocyclization of hanphyllin with N-bromosuccinimide

Cited by 4 publications

References 3 publications

Stereocontrolled acid cyclization of (+)-hanphillin

Stereocontrolled acid cyclization of (+)-hanphillin

Ti-catalyzed transannular cyclization of epoxygermacrolides. Synthesis of antifungal (+)-tuberiferine and (+)-dehydrobrachylaenolide

Biomimetic cyclization of Е,Е-germacranolide (+)-hanphilline

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