Totalsynthese von Myrtucommulon A

Müller, Hans; Paul, Michael; Hartmann, David; Hüch, Volker; Blaesius, Dagmar; Koeberle, Andreas; Werz, Oliver; Jauch, Johann

doi:10.1002/ange.200903906

Cited by 5 publications

(3 citation statements)

References 43 publications

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“…Our racemic synthesis [7] started from syncarpic acid (3) [9] and led to MC A (1) as a mixture of three stereoisomers (i.e., two enantiomers and one meso compound) through the reaction between isobutylidene syncarpic acid (4) [10] and double deprotonated isobutyryl phloroglucinol (5) [11] (see Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Later, MC A (1) was also found in other species of the myrtaceae family. [7] Interestingly, the synthetic MC A (1), which was a mixture of three stereoisomers, showed the same pharmacological activity as natural MC A (1) with respect to mPGES1-inhibition and induction of apoptosis. [7] Interestingly, the synthetic MC A (1), which was a mixture of three stereoisomers, showed the same pharmacological activity as natural MC A (1) with respect to mPGES1-inhibition and induction of apoptosis.…”

Section: Introductionmentioning

confidence: 92%

“…[2][3][4] We became interested in the myrtucommulones because of their anti-inflammatory [5] and cytotoxic [6] activities and developed a short and efficient synthesis for MC A (1) and other members of this compound family. [7] This posed the question as to the stereoisomeric composition of MC A (1) that was isolated from Myrtus communis. [7] This posed the question as to the stereoisomeric composition of MC A (1) that was isolated from Myrtus communis.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Synthesis of Myrtucommulone A

2013

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Myrtucommulone A (1), which was isolated from myrtle and other species of the myrtaceae family, was synthesized through an enantioselective Michael addition of isobutyryl phloroglucinol (5) to isobutylidene syncarpic acid (4) that was induced by a chiral Al–Li–BINOL (1,1′‐bi‐2‐naphthol) complex [(S,S)‐ALB]. Because there is significant steric crowding in Michael acceptor 4, myrtucommulone A (1) was obtained with an ee value of 70 % along with meso‐1 in 77 % chemical yield.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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Enantioselective Synthesis of Myrtucommulone A

2013

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Chemistry and Biology of the Polycyclic Polyprenylated Acylphloroglucinol Hyperforin

Richard

2013

Eur J Org Chem

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(+)‐Hyperforin (1) is a polyprenylated acylphloroglucinol (PPAP) natural product isolated in 1971 from Hypericum perforatum. Also known as St. John's wort, Hypericum perforatum is a popular medicinal plant because of its antidepressant properties. (+)‐Hyperforin (1) is the main component of the plant and has attracted the interest of the scientific community since it was identified as the agent responsible for the antidepressant activity. The subsequent discovery that it also displayed a wide range of biological activities triggered the interest of synthetic chemists because of its appealing, compact molecular structure. This microreview presents an overview of the synthetic studies reported so far for the racemic and enantioselective syntheses of (+)‐hyperforin (1) and analogues, and attempts to shed light on the intriguing structure–activity relationships (SARs) of the natural product.

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Bioactive Phloroglucinyl Heterodimers: The Tautomeric and Rotameric Equlibria of Arzanol

Rastrelli¹,

Bagno²,

Appendino

et al. 2016

Eur J Org Chem

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Arzanol (1) exemplifies a large number of heterodimeric bioactive natural products based on an alkylidene‐bridged β‐dicarbonyl‐acylphloroglucinyl structural motif. The NMR spectra of these compounds are complicated by tautomeric and rotational equilibria that, despite growing synthetic and biomedical interest in the area, have not been systematically investigated. By combining information from NMR spectroscopy and DFT calculations, we have comparatively characterized the solution structures and conformations of the anti‐inflammatory agent arzanol (1), its inactive monomethyl derivative 4, and its corresponding homodimers [helipyrone (5) and demethylmallotojaponin C (6)]. The results highlight the relevance of a network of intramolecular hydrogen bonds for the tautomeric and rotameric equilibria of these compounds, with arzanol (1) existing in two almost equally populated rotameric forms of a 2‐pyrone tautomer, and its phloroglucinyl homodimer 6 in four major forms. Conversely, the monomethyl derivative 4 of arzanol and its dipyrone homodimer 5 exist in essentially a single solution form. Interestingly, this conformational bias was associated with a marked decrease of bioactivity.

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Totalsynthese von Myrtucommulon A

Cited by 5 publications

References 43 publications

Enantioselective Synthesis of Myrtucommulone A

Enantioselective Synthesis of Myrtucommulone A

Chemistry and Biology of the Polycyclic Polyprenylated Acylphloroglucinol Hyperforin

Bioactive Phloroglucinyl Heterodimers: The Tautomeric and Rotameric Equlibria of Arzanol

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