Clavicipitic acid, a new 4-substituted indolic amino acid obtained from submerged cultures of the ergot fungus

Robbers, James E.; Floss, Heinz G.

doi:10.1016/s0040-4039(01)88031-x

Cited by 50 publications

(15 citation statements)

References 4 publications

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“…36,37 This clavine alkaloid is structurally characterized by the presence of the same azepinoindole core as in aurantioclavine ( 2 ). In 2010, Jia et al established that the relative configurations of cis - ( 1b ) and trans - ( 1a ) clavicipitic acid were incorrectly assigned in the literature and noted that their assignment in past literature should in fact be reversed.…”

Section: Synthetic Approaches To Rearranged Clavine Alkaloids Covementioning

confidence: 99%

Total synthesis, biosynthesis and biological profiles of clavine alkaloids

McCabe

Wipf

2016

Org. Biomol. Chem.

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This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids. Recent biosynthetic insights have laid the groundwork for a better understanding of the diverse biological pathways leading to these indole derivatives. Ergot alkaloids were among the first fungal-derived natural products identified, inspiring pharmaceutical applications in CNS disorders, migraine, infective diseases, and cancer. Pergolide, for example, is a semi-synthetic clavine alkaloid that has been used to treat Parkinson’s disease. Synthetic activities have been particularly valuable to facilitate access to rare members of the Clavine family and empower medicinal chemistry research. Improved molecular target identification tools and a better understanding of signaling pathways can now be deployed to further extend the biological and medical utility of Clavine alkaloids.

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Section: Synthetic Approaches To Rearranged Clavine Alkaloids Covementioning

confidence: 99%

Total synthesis, biosynthesis and biological profiles of clavine alkaloids

McCabe

Wipf

2016

Org. Biomol. Chem.

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“…In 1969, Robbers and Floss isolated an ergot alkaloid from Claviceps strain and named it clavicipitic acid. On the basis of mass spectra, 1 H NMR, and biosynthetic study, they proposed the structure 1 (Figure ) . In 1973, Waight and co‐workers also isolated the same compound from Claviceps fusiformis , and they proposed the revised structure for clavicipitic acid ( 2 ) .…”

Section: Introductionmentioning

confidence: 99%

Strategies for the Total Synthesis of Clavicipitic Acid

Ito

Tahara

Shibata

2016

Chemistry A European J

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Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4-substituted gramine derivatives and 4-substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates.

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“…In 1969, Robbers and Floss isolated an ergot alkaloid from Claviceps strain and named it clavicipitic acid. On the basis of mass spectra, 1 HNMR, and biosynthetic study,t hey proposed the structure 1 (Figure 1). [1] In 1973, Waight and co-workers also isolated the same compound from Claviceps fusiformis, and they proposed the revised structure for clavicipitic acid (2).…”

Section: Introductionmentioning

confidence: 99%