Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Ishigami, Ken

doi:10.1271/bbb.80877

Cited by 20 publications

(11 citation statements)

References 81 publications

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“…Hzla01-1 Marine-derived fungus [38] Phomolide C (61) Phomopsis sp. B27 Endophytic fungus [39] Z-4, 6,4,5,6,9, 10-hexahydrooxecin-2-one (48) Tubercularia sp. TF5 Endophytic fungus [40] Achaetolide (49) Ophiobolus sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…(2). The extended alkyl side chains, usually containing an odd number of carbons (3)(4)(5)(6)(7)(8)(9), are typically located at C-9 of the lactone ring.…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

“…Carbon-carbon bond forming reactions, such as transition metalpromoted coupling and olefin metathesis, have been widely applied in producing cyclic compounds [6]. Macrolactonization is also a popular method to construct medium-sized lactones or macrolones [60].…”

Section: Strategies For Construction Of the 10-membered Lactonementioning

confidence: 99%

“…Sch 642305 (57) exhibited inhibitory activity against bacterial DNA primase enzyme with an EC 50 primase (dnaG) is a DNA-dependent RNA polymerase, which is an attractive target for antibacterial drug discovery [197]. Compound 57 is thought to provide an alternative treatment for infectious diseases [6]. Dictyosphaeric acid A (59) showed weak antibacterial activity towards Gram positive bacteria, including methicillinsensitive Staphylococcus aureus, MRSA, vancomycin-resistant Enterococcus faecium and Candida albicans, while dictyosphaeric acid B (60) showed no antimicrobial activity at 50 μg well -1 [30].…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…The first one covered synthetic studies on selected naturally occurring ten-membered lactones [5]. The second focused on synthetic approaches to three 10-membered lactones: mueggelone (39), microcarpalide (43), and Sch 642305 (57) [6]. The third review summarized the biological and synthetic studies of the metabolites belonging to the decarestrictine family [7].…”

Section: Introductionmentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…(2). The extended alkyl side chains, usually containing an odd number of carbons (3)(4)(5)(6)(7)(8)(9), are typically located at C-9 of the lactone ring.…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

Section: Strategies For Construction Of the 10-membered Lactonementioning

confidence: 99%

Section: Antibacterial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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ChemInform Abstract: Synthetic Studies of Natural 10‐Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Ishigami

2010

ChemInform

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Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

Kurtán

Yang

et al. 2011

Eur J Org Chem

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Cytospolides A-E (1-5), five new nonanolides with an unprecedented 15-carbon skeleton with the unique chemical feature of a C-2 methyl group, were isolated from the endophytic fungus Cytospora sp. The structures were elucidated by spectroscopic analysis, chemical interconversion, and single-crystal XRD. The solution and solid state conformers were compared by experimental methods (X-ray, NMR) and solvent and gas phase DFT calculations. The absolute configurations were assigned by time dependent (TD)-DFT calculations of CD spectra, including solution and solid state CD/

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Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Cited by 20 publications

References 81 publications

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

ChemInform Abstract: Synthetic Studies of Natural 10‐Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities

Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

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