Phytotoxic Sesterterpene, 11-Epiterpestacin, from<i>Bipolaris sorokiniana</i>NSDR-011

Nihashi, Yoichiro; Lim, Chi-Hwan; Tanaka, Chihiro; Miyagawa, Hisashi; Ueno, Tamio

doi:10.1271/bbb.66.685

Cited by 42 publications

(37 citation statements)

References 11 publications

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“…A good illustration resides in the elucidation of the structure of the liminoid insect antifeedant azadirachtin. A recent example is a total synthesis reported by Chan and Jamison at MIT [168] that showed that the proposed structure 58 of siccanol [169] was incorrect and that the natural product is identical to (À)terpestacin (59). [161] By the mid-1980s, however, the isolation of some structurally related compounds began to suggest that some elements of the central core were inaccurate.…”

Section: Methodsmentioning

confidence: 99%

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

2005

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Over the course of the past half century, the structural elucidation of unknown natural products has undergone a tremendous revolution. Before World War II, a chemist would have relied almost exclusively on the art of chemical synthesis, primarily in the form of degradation and derivatization reactions, to develop and test structural hypotheses in a process that often took years to complete when grams of material were available. Today, a battery of advanced spectroscopic methods, such as multidimensional NMR spectroscopy and high-resolution mass spectrometry, not to mention X-ray crystallography, exist for the expeditious assignment of structures to highly complex molecules isolated from nature in milligram or sub-milligram quantities. In fact, it could be argued that the characterization of natural products has become a routine task, one which no longer even requires a reaction flask! This Review makes the case that imaginative detective work and chemical synthesis still have important roles to play in the process of solving nature's most intriguing molecular puzzles.

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Section: Methodsmentioning

confidence: 99%

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

2005

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“…16 The spectroscopic characteristics and the specific ro tation of the 11 epiterpestacin 2 isolated by us almost coincided with those reported in the literature. 17 The last component of the extract, compound 3, was identified as β nitropropionic acid, according to X ray diffraction data. 18 Compound 1 possesses an antimicrobial activity against Staphylococcus aureus and Bacillus subtilis (MIC = 12.5 µg mL -1 ) and exhibits a cytotoxic action on the developing eggs of sea urchin Strongylocentrotus intermedius (MIC 50 = 40 µg mL -1 ).…”

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confidence: 99%

Metabolites of the marine fungus Humicola fuscoatra KMM 4629

et al. 2004

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A new sesquiterpene of the caryophyllene series, fuscoatrol А (1), and known compounds, 11 epiterpestacin (2) and β nitropropionic acid (3), were isolated from the marine fungus Humicola fuscoatra (Traaen) KMM 4629 associated with the Kuril colonial ascidium. The structure of 1 was established on the basis of X ray diffraction data and 2D NMR spectroscopy. The antimicrobial and cytotoxic activities of compounds 1-3 were studied.

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“…However, when we obtained a sample of synthetic epi-C11-terpestacin it was determined that its spectra did not match that of isolated siccanol but rather that of terpestacin itself. 40 Macrocyclization via an intramolecular allylation, followed by methylation and α-oxidation led to the completed synthesis of terpestacin and epi-C11-terpestacin.…”

Section: Enantioselective Reactionsmentioning

confidence: 99%

Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes

2007

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Nickel-catalysed reductive coupling reactions of alkynes have emerged as powerful synthetic tools for the selective preparation of functionalized alkenes. One of the greatest challenges associated with these transformations is control of regioselectivity. Recent work from our laboratory has provided an improved understanding of several of the factors governing regioselectivity in these reactions, and related studies have revealed that the reaction mechanism can differ substantially depending on the ligand employed. A discussion of stereoselective transformations and novel applications of nickel catalysis in coupling reactions of alkynes is also included.

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Phytotoxic Sesterterpene, 11-Epiterpestacin, fromBipolaris sorokinianaNSDR-011

Cited by 42 publications

References 11 publications

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

Metabolites of the marine fungus Humicola fuscoatra KMM 4629

Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes

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