- Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes
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A Diels-Alder reaction of novel inner-outer-ring 1,3-silyloxydienes 5-8 with a variety of dienophiles to afford highly functionalized polycyclic structures is reported. The inner-outer-ring 1,3-silyloxydienes 5-8 containing five- to seven-membered carbocyclic and heterocyclic rings were prepared in a single reaction vessel from 2-acetylcyclocarbonyls in quantitative yields. The Diels-Alder reaction with 1,4-benzoquinone (BQ), dimethyl acetylenedicarboxylate (DMAD), and methyl vinyl ketone (MVK) proceeded smoothly at room temperature, affording functionalized polycyclic naphthols, phenols, and enones with high regioselectivity and good yields (39-75%). Moreover, dienes 5-8 also reacted in a hetero-Diels-Alder reaction with benzaldehyde (BA) and N-benzylideneaniline (NBA) in the presence of catalytic amounts of ZnCI2, affording substituted polycyclic pyranones and pyridinones in good yields (40-93%). Overall, our synthetic strategy provides straightforward access to an interesting set of polycyclic structures useful for natural and nonnatural product synthesis.
- Sestelo,Del Mar Real,Sarandeses
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p. 1395 - 1402
(2007/10/03)
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- Regioselective synthesis and acylation of cyclic bis-(trimethylsiloxy)- 1,3-dienes - New and versatile 1,3-dianion synthons
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Cyclohexanone-derived bis-(trimethylsiloxy)-1,3-dienes were regioselectively prepared by the use of different silylating systems. These dienes represent new and versatile 1,3-dianion synthons in Lewis-acid catalyzed acylation reactions.
- Langer, Peter,Schneider, Toni
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p. 497 - 500
(2007/10/03)
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- Domino reaction of 1,3-bis(trimethylsilyloxy)-1,3-dienes with oxalyl chloride: General and stereoselective synthesis of γ-alkylidenebutenolides
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The Lewis acid catalyzed cyclization of oxalyl chloride with 1,3-bis-(trimethylsilyloxy)-1,3-dienes 3, derived from 1,3-dicarbonyl compounds 1, provides a new and general approach for the synthesis of γ-alkylidenebutenolides 4, a pharmacologically and syn
- Langer, Peter,Schneider, Toni,Stoll, Martin
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p. 3204 - 3214
(2007/10/03)
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- Synthesis of polycyclic structures by Diels-Alder reaction using inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes
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In this paper we describe regioselective one-pot preparations of inner- outer-ring 1,3-bis[trimethylsilyloxy]dienes and their Diels-Alder reactions with electron-deficient dienophiles. The dienes were prepared in quantitative yield, and the Diels-Alder reactions proceeded smoothly, regioselectively and with good yields, allowing efficient construction of highly functionalized polycyclic skeletons such as naphthofurans, benzofurans and various carbocycles present in natural and non-natural products.
- Sestelo, Jose Perez,Del Mar Real,Mourino, Antonio,Sarandeses, Luis A.
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p. 985 - 988
(2007/10/03)
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- Utilisation de Me3SiI prepare in situ pour l'obtention de bis(trimethylsiloxy-1,3) diene-1,3
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The in situ generation of iodotrimethylsilane, in the presence of triethylamine, is a convenient route to 1,3-bis(trimethylsiloxy)-1,3-diene.
- Babot, O.,Cazeau, P.,Duboudin, F.
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p. C57 - C60
(2007/10/02)
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- Reactions of Trialkylsilyl Trifluoromethanesulfonates, III. - Synthesis of 1,3-Bis(trimethylsiloxy)-1,3-dienes and 3-Trimethylsiloxy-2-butenoates Silylated in Position 4
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Bis(trimethylsiloxy)-1,3-dienes 5a - n are obtained by reaction of 1,3-dicarbonyl compounds 1 with trimethylsilyl trifluoromethanesulfonate (2) in the presence of triethylamine (3).The silyl enol ether 8 is silylated by 2/3 to yield 1,3-bis(trimethylsiloxy)-1,3-butadiene (5o).Depending on the conditions, alkyl 3-oxobutanoates 12 react with 2/3 to give the γ-silylated alkyl 3-trimethylsiloxy-2-butenoates 15 or 16.
- Kraegeloh, Konrad,Simchen, Gerhard,Schweiker, Kurt
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p. 2352 - 2362
(2007/10/02)
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