Synthesis of methyl 2-oxo-5-vinyl-2,5-tetrahydrofuran-3-carboxylate

Silvestri, Maximilian A.; He, C.; Khoram, Anita; Lepore, Salvatore D.

doi:10.1016/j.tetlet.2005.12.114

Cited by 7 publications

(4 citation statements)

References 14 publications

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“…The solvent was evaporated, and the crude product was purified by flash column chromatography on silica gel (200–300 mesh, petroleum ether/ethyl acetate, 20:1) to obtain γ-lactone 4 as a pair of unseparable diastereoisomers (1:1, 167 mg, 98%). The NMR data coincided with the literature …”

Section: Experimental Sectionsupporting

confidence: 87%

TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles

2013

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Section: Experimental Sectionsupporting

confidence: 87%

TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles

2013

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“…Treatment of the acetate precursor 1a or the carbonate 1b under reaction conditions analogous to those used to cyclize the lactam precursors gave only degradation products (Table , entries 1 and 2). On the other hand, in the absence of base, 1b gave the undesired rearranged lactone 3 as the only isolated product (Table , entry 3) …”

Section: Resultsmentioning

confidence: 99%

New Picropodophyllin Analogs via Palladium-Catalyzed Allylic Alkylation−Hiyama Cross-Coupling Sequences

et al. 2008

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Unsaturated malonyl esters underwent Pd-catalyzed intramolecular allylic alkylation to give 4-vinyl-substituted gamma-lactones. In contrast to the formerly studied cyclization of malonamides, this reaction could be achieved only with a substrate incorporating a suitably positioned silicon moiety, which directs the ionization toward the desired eta(3)-allylpalladium complex. The resulting 4-[dimethyl-(2-thienyl)silylvinyl]lactone could be subsequently engaged into Hiyama couplings with various iodoarenes, to give the corresponding 4-(alpha-styryl)-gamma-lactones. The use of a specifically substituted iodoarene generated an advanced tetracyclic lactone intermediate incorporating rings A-D of lignans belonging to the podophyllotoxin family. Subsequent electrophilic aromatic substitution with a variety of electron-rich arenes afforded the target picropodophyllin analogs.

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“…Synthesis of the F ring building block 5 commenced with ring opening of easily accessible γ-vinyl butyrolactone 8 with methallylsilane 9 in the presence of Meerwein’s salt to give diene 10 in good yield as a single isomer (Scheme ) . In the next step, a regioselective asymmetric dihydroxylation under carefully optimized reaction conditions gave access to lactone 11 with useful levels of regioselectivity (4:1) and 98% ee .…”

mentioning

confidence: 99%

Synthetic Studies Toward Pectenotoxin 2. Part II. Synthesis of the CDE and CDEF Ring Systems

2008

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Synthesis of methyl 2-oxo-5-vinyl-2,5-tetrahydrofuran-3-carboxylate

Cited by 7 publications

References 14 publications

TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles

TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles

New Picropodophyllin Analogs via Palladium-Catalyzed Allylic Alkylation−Hiyama Cross-Coupling Sequences

Synthetic Studies Toward Pectenotoxin 2. Part II. Synthesis of the CDE and CDEF Ring Systems

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