Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C<sub>10</sub>−C<sub>22</sub> Fragment

Aho, Jatta E.; Salomäki, Elina; Rissanen, Kari; Pihko, Petri M.

doi:10.1021/ol8015868

Cited by 34 publications

(11 citation statements)

References 40 publications

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.39–7.28 (m, 5H), 5.33 (s, 1H), 5.28 (d, J = 1.3 Hz, 1H), 4.54 (s, 2H), 4.15 (d, J = 1.0 Hz, 2H), 4.13 (s, 2H). The physical and spectral data were consistent with those previously reported …”

Section: Methodssupporting

confidence: 91%

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Wang

et al. 2019

J. Org. Chem.

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Twofold unsymmetrical C−Si bond bifunctionalization of 2,6-di(trimethylsilyl) benzyl alcohols has been achieved in one pot via sequential [1,4]-Csp 2 to O-silyl migration. The hydroxyl group functions as an "on−off−on" switch to control two successive silyl migrations, and 4,7dimethyl-o-phenanthroline ligand favors cleavage of the endocyclic C−Si bond. Diverse Csp 3 /Csp 3 or Csp 2 /Csp 3 electrophiles can be installed at the 2-and 6-positions. This approach was used to chemoselectively functionalize the three C−Si bonds of 2,4,6-tri(trimethylsilyl) benzyl alcohol, transforming it into isochroman derivatives. The approach even works as a five-component reaction to construct complex symmetric structures.

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Section: Methodssupporting

confidence: 91%

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Wang

et al. 2019

J. Org. Chem.

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“…Compound 16 has been described by Pihko and co-workers as an intermediate in the synthesis of the natural product class of pectenotoxins; intermediate 16 was synthesised in four steps in an overall yield of 28%. 14 In such cases, it is quite satisfying that our approach seems to be more efficient and concise as the same product can be realised in two steps and in 79% yield.…”

Section: The 'Second Generation' Of 14-hydrovinylation Processesmentioning

confidence: 80%

“…compound 12, in a multicomponent reaction is shown in Scheme 9. A short reaction sequence via hydroxy-substituted 1,3-dicarbonyl intermediate 13 led to the assembly of racemic hepialone (14) in good overall yield. 12…”

Section: Methodsmentioning

confidence: 99%

Cobalt(I)-Catalysed Reactions for the Synthesis of Acyclic 1,4-Dienes - Genesis of Two Synthetic Methods

Hilt¹

2011

Synlett

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The search for atom-economic carbon-carbon bondforming reactions initiated by low-valent cobalt complexes has led to two reactions that generate acyclic 1,4-dienes: the 1,4-hydrovinylation reaction of a terminal alkene with a 1,3-diene and the Alderene reaction of a terminal alkene with an internal alkyne.The regioselective cobalt-catalysed Diels-Alder reaction of an alkyne and a 1,3-diene for the synthesis of cyclic 1,4-dienes led to its application in the synthesis of 1,3-dicarbonyl derivatives upon ozonolysis. Through applications of the cobalt-catalysed 1,4-hydrovinylation reaction, the synthesis of 1,3-or 1,4-dicarbonyl derivatives can be accomplished in a substrate-controlled process. For instance, 2,3-dimethylbuta-1,3-diene leads to acyclic 1,4-dienes via the cobalt-catalysed 1,4-hydrovinylation reaction which can then be converted into 1,3-carbonyls by ozonolysis. In contrast, the use of 2-(trimethylsiloxy)buta-1,3-diene generates g,d-unsaturated ketones, which can be converted into 1,4-dicarbonyl derivatives upon ozonolysis. Recently, studies into the synthesis of different types of polycarbonyl compounds in which the distance between the carbonyl groups can be altered have been initiated.

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“…It actually permits control of the stereogenic centers in advance thanks to asymmetric epoxidation reactions, and only needs acid or basic conditions, usually at room temperature, to induce the cyclization step. Thus, the literature is rich in acid catalyzed epoxide opening cyclizations, using either Brønsted acids such as PPTS 19 or CSA, or Lewis acids as the standard BF 3 .Et 2 O. Nevertheless, some unusual acids were also studied, as well as basic media, and all these efforts will be presented herein.…”

Section: Scheme 3: Homoallylic Alcohol Resolution and Cyclizationmentioning

confidence: 99%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C₁₀−C₂₂ Fragment

Abstract: A highly stereocontrolled and efficient synthesis for a fully functionalized C 10-C 22 fragment of pectenotoxin 2 is described using a convergent sequence involving a stereoselective methylation of beta-hydroxyketone as a key step.

Cited by 34 publications

References 40 publications

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

Cobalt(I)-Catalysed Reactions for the Synthesis of Acyclic 1,4-Dienes - Genesis of Two Synthetic Methods

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

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Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C10−C22 Fragment

Abstract: A highly stereocontrolled and efficient synthesis for a fully functionalized C 10-C 22 fragment of pectenotoxin 2 is described using a convergent sequence involving a stereoselective methylation of beta-hydroxyketone as a key step.

Cited by 34 publications

References 40 publications

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp2 to O-Silyl Migration

Cobalt(I)-Catalysed Reactions for the Synthesis of Acyclic 1,4-Dienes - Genesis of Two Synthetic Methods

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

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Product

Resources

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Synthetic Studies Toward Pectenotoxin 2. Part I. Stereocontrolled Access to the C₁₀−C₂₂ Fragment

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration

One-Pot Twofold Unsymmetrical C–Si Bond 2,6-Bifunctionalization of Arenes via Sequential [1,4]-Csp² to O-Silyl Migration