Fungal extractives. IX. Synthesis of the velleral skeleton and a total synthesis of pyrovellerolactone

Froborg, Jan; Magnusson, Göran; Thorén, Svante

doi:10.1021/jo00899a017

Cited by 20 publications

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References 17 publications

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“…1 h). The crude diene acetal aldehyde [e.g., from 16A: NMR 9.44 (s, 1 H), 6.88 (d, 1 H, J = 5.5 Hz), 6.28 (s, broad, 1 H), 5.47 ppm (m, 1 H)] was treated with a trace of p-toluenesulfonic acid in acetone/water (20/1,10 mL) for 2 h. After neutralization (K2CO3), the solvent was evaporated and the residue extracted with ether. After drying and evaporation of the ether phase, the residue was chromatographed (S1O2 column, 12 g; hexane/ethyl acetate, 7/3).…”

Section: Methodsmentioning

confidence: 99%

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Fungal extractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures

Froborg¹,

Magnusson²

1978

J. Am. Chem. Soc.

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Velleral, vellerolactone, and pyrovellerolactone, three hydroazulenic sesquiterpenoids from basidiomycetes of the genus Lactarius, have been prepared by cycloaddition of enamines of bicyclo[3.3.0]octanones to 4-substituted tetrolic esters, followed by fission of the four-membered ring and subsequent hydrogenolytic deamination with diborane. Further functional group manipulation gave the natural compounds. X-ray crystallographic analyses of key synthetic intermediates, together with spectroscopic data on synthetic stereoisomers of the natural compounds, necessitate a revision of the earlier suggested structures for all three title compounds. Molecular mechanics calculations revealed that the configuration of a methyl group on carbon atom 3 in the seven-membered ring has a profound effect on the conformation of the hydroazulenic ring system. These findings are corroborated by the X-ray crystallographic results.

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Section: Methodsmentioning

confidence: 99%

“…Diacetylanhydroaglycon (4) of Oleandomycin. The anhydroaglycon of 1 was prepared from 1 (0.85 g) according to modified procedures of Hochstein et al 5 The yield was 0.072 g, mp 219-220 °C (lit.5 mp 228-230 0 C). The diacetate 4 was prepared from the anhydroaglycon (0.05 g) by treating with acetic anhydride (1 mL) and pyridine (1 mL) at 60 °C.…”

Section: Methodsmentioning

confidence: 99%

Fungal extractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures

Froborg¹,

Magnusson²

1978

J. Am. Chem. Soc.

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Total Synthesis of Sesquiterpenes, 1970‐79

Heathcock¹,

Graham²,

Pirrung³

et al. 1982

Total Synthesis of Natural Products

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Electrochemistry of Heterocycles

Moinet¹

2004

Encyclopedia of Electrochemistry

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The sections in this article are Overview on the Electrochemistry of Heterocycles Electrosyntheses of Heterocycles Anodic Cyclizations Cathodic Cyclizations Electrochemical Behavior of Heterocycles Oxidation of Heterocycles Reduction of Heterocycles Oxidative Cyclizations at the Anode Intramolecular Cyclizations Carbon–Carbon Bond Formation Carbon–Heteroatom Bond Formation Heteroatom–Heteroatom Bond Formation Intermolecular Coupling Heterocoupling Reactions Homocoupling Reactions Reductive Cyclization at the Cathode Intramolecular Cyclization Carbon–Carbon Bond Formation Carbon–Heteroatom Bond Formation Heteroatom–Heteroatom Bond Formation Intermolecular Cyclization Heterocoupling Reactions Homocoupling Reaction Anodic Oxidation of Heterocycles Double Bond Formation Functionalization of Heterocycles Methoxylation Reactions Acetoxylation Reactions Hydroxylation Reactions Cyanation Reactions Halogenation Reactions Trifluoromethylation Reactions Intramolecular Coupling Reactions Dimerization Reactions Ring Expansions Ring Contractions Ring Opening Cathodic Reduction of Heterocycles Electroreductive Hydrogenation of Double Bonds Functionalization of Heterocycles Addition Reactions Substitution Reactions Intramolecular Coupling Reactions Dimerization Reactions Ring Expansions Ring Contractions Ring Opening

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Fungal extractives. IX. Synthesis of the velleral skeleton and a total synthesis of pyrovellerolactone

Cited by 20 publications

References 17 publications

Fungal extractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures

Fungal extractives. 12. Construction of the vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone. Revised structures

Total Synthesis of Sesquiterpenes, 1970‐79

Electrochemistry of Heterocycles

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