Enantioselective Total Synthesis of Hyperforin

Sparling, Brian A.; Moebius, David C.; Shair, Matthew D.

doi:10.1021/ja312150d

Cited by 107 publications

(85 citation statements)

References 75 publications

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“…The structures published in [20] [21] are identical to the structure of substance proposed in [16], and it is proven by two decisive analyses [20] [21]. Publications [20] and [21] support the earlier elucidation of the relative and absolute stereochemistry of hyperforin by X-ray crystallography, as published in [15] and [16].…”

Section: Stereochemistry Of Hyperforin Proposed By Brondzsupporting

confidence: 57%

“…Figure 13 shows the structure presented by Shimizu et al [21] and that of the structure published [16], for comparison. Proving that the X-ray structure of hyperforin in [16] is identical to that of the synthetic structures in [20] and provides the best evidence for the accuracy of the structure given in [16].…”

Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 89%

“…In publication [23] was adopted the formula of major B isomer of hyperforin as it presented in Figure 3, and formula of hyperforin Figure 12 as was presented in [20], and formula of hyperforin Figure 13 as was presented in [21]. In all of these publications, the same relative and absolute configuration for the major isomer of hyperforin is 1R, 5R, 7S, 8R, which follows from publications [15] and [16].…”

Section: Discussionmentioning

confidence: 99%

“…Structures presented in Figure 12 [20] as hyperforin and hyperforin Figure 13(1) in [21] have the same IUPAC name and chirality as hyperforin in Figures 3(3) and Figure 13(4) [16]. The structures published in [20] [21] are identical to the structure of substance proposed in [16], and it is proven by two decisive analyses [20] [21]. Publications [20] and [21] support the earlier elucidation of the relative and absolute stereochemistry of hyperforin by X-ray crystallography, as published in [15] and [16].…”

Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 99%

“…Structure of hyperforin presented in [20]. (Name of the substance and numbering of C atoms following IUPAC convention were added by the author of this paper).…”

Section: Challenging the Relative And Absolute Stereochemistry Of Hypmentioning

confidence: 99%

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Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Brondz¹

2017

IJAMSC

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Relative and absolute stereochemistry for hyperforin has been proposed by Brondz et al. was supported and new isomer of hyperforin-perforatrin has been discovered. Relative and absolute stereochemistry for perforatrin was proposed and elucidated by using gas-chromatography mass-spectrometry with supersonic molecular beams (SMB). The possibility of the existence of ambiguities in chirality as a hypothesis for the existence, and a new understanding, of chiral substances with shifting chirality is presented.

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Section: Stereochemistry Of Hyperforin Proposed By Brondzsupporting

confidence: 57%

Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 99%

“…Structure of hyperforin presented in [20]. (Name of the substance and numbering of C atoms following IUPAC convention were added by the author of this paper).…”

Section: Challenging the Relative And Absolute Stereochemistry Of Hypmentioning

confidence: 99%

See 3 more Smart Citations

Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Brondz¹

2017

IJAMSC

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Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Rosenstein¹

2022

Organic Reactions

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This chapter describes the use of allyl‐ and vinylstannane reagents for a variety of radical‐based transformations. The processes discussed include direct addition of radicals to allyl‐ and vinylstannanes, multicomponent or multistep cascade reactions that terminate with an intermolecular allylation or vinylation, cyclizations onto allyl‐ or vinylstannane moieties, and allylstannylation reactions. Allylation reactions have provided a framework for the exploration of stereoselective radical reactions, and models for explaining the stereoselectivity obtained by a number of approaches are presented. Examples are provided to illustrate the scope of applications of allyl‐ and vinylstannane radical reactions in synthesis, as well as the ways that the newly introduced allyl and vinyl groups have been subsequently manipulated. A comparison is made to radical allylation and vinylation reactions that employ non‐tin‐based reagents.

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Neurotrophe Naturstoffe – ihre Chemie und Biologie

Lacoske

Theodorakis

2013

Angewandte Chemie

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Neurodegenerative Erkrankungen und Rückenmarksverletzungen betreffen weltweit etwa 50 Millionen Menschen und verursachen Gesundheitskosten von insgesamt mehr als 600 Milliarden Dollar pro Jahr. Nervenwachstumsfaktoren, d. h. Neurotrophine, sind potenzielle Therapeutika für diese Erkrankungen, denn sie können die Regeneration von Nerven fördern. Durchschnittlich 500 Publikationen jährlich belegen die Bedeutung der Neurotrophine in den biomedizinischen Wissenschaften und ihr Potenzial für therapeutische Anwendungen. Allerdings ist die klinische Verwendung von Neurotrophinen wegen ihres schlechten pharmakokinetischen Profils stark eingeschränkt. Niedermolekulare Verbindungen, die die neurotrophe Aktivität modulieren, bieten hingegen einen vielversprechenden Therapieansatz bei neurologischen Erkrankungen. Die Natur hat für eine beeindruckende Zahl von Naturstoffen mit starken neurotrophen Wirkungen gesorgt. Die aktuellen Strategien zur Synthese dieser Verbindungen sowie deren Fähigkeit, das Wachstum und die Erneuerung von Nervenzellen zu induzieren, bilden den Schwerpunkt dieses Aufsatzes. Es ist davon auszugehen, dass neurotrophe Naturstoffe nicht nur als Leitstrukturen in der Wirkstoffentwicklung genutzt werden können, sondern auch für das nächste große Projekt der Biomedizin: die Kartierung der Hirnaktivität (BAM, Brain Activity Map).

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Enantioselective Total Synthesis of Hyperforin

Cited by 107 publications

References 75 publications

Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Neurotrophe Naturstoffe – ihre Chemie und Biologie

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