Ketene Acetal and Spiroacetal Constituents of the Marine Fungus Aigialus parvus BCC 5311
Pornrapee VongvilaiMasahiko IsakaPrasat KittakoopPrasert SrikitikulchaiPalangpon KongsaereeYodhathai Thebtaranonth
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Abstract:
Aigialone (1) and aigialospirol (2), two structurally unique compounds, were isolated from the mangrove fungus Aigialus parvus BCC 5311. The structure of the new ketene acetal 1 was elucidated by spectral analysis, and its relative stereochemistry was determined by X-ray crystallography. The stereochemistry of aigialospirol (2), elucidated by NMR spectral analysis, suggested that this compound is possibly derived from hypothemycin (3), a metabolite previously isolated from this same fungus.Keywords:
Spectral Analysis
Aldol reaction
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Abstract A highly useful method is established for the stereoselective synthesis of (Z)-α-fluoroacrylates from various aldehydes and fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal in the presence of a Lewis base catalyst. The ketene acetal, easily prepared from ethyl fluoroacetate, affords α-fluoroacrylates in high yields with excellent Z stereoselectivities under mild conditions.
Trimethylsilyl
Fluoroacetate
Base (topology)
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A new, facile, and high-yield synthesis of ketene acetals derived from readily available and inexpensive starting materials has been developed. For example, an α,β-unsaturated aldehyde can be condensed with an alkane diol to afford a 2-vinyl substituted cyclic acetal. This latter compound can be converted to the desired cyclic ketene acetal by isomerization of the double bond in the presence of tris(triphenylphosphine)ruthenium(II) dichloride. Good to excellent yields of cyclic ketene acetals were obtained employing this method. The novel monomers were fully characterized by IR, NMR, and by elemental analysis. © 1996 John Wiley & Sons, Inc.
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Tricyclic
Arabinose
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A new, facile, and high-yield synthesis of ketene acetals derived from readily available and inexpensive starting materials has been developed. For example, an α,β-unsaturated aldehyde can be condensed with an alkane diol to afford a 2-vinyl substituted cyclic acetal. This latter compound can be converted to the desired cyclic ketene acetal by isomerization of the double bond in the presence of tris(triphenylphosphine)ruthenium(II) dichloride. Good to excellent yields of cyclic ketene acetals were obtained employing this method. The novel monomers were fully characterized by IR, NMR, and by elemental analysis. © 1996 John Wiley & Sons, Inc.
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Abstract Durch Umsetzung der cyclischen Acetale (I) mit den Ketenacetalen (II) in Gegenwart von Titantetrachlorid erhält man in stereospezifischer Reaktion fast ausschließlich die Addukte (III).
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Carbenoid
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