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Costaclavin

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Costaclavin
Names
IUPAC name
6,8β-Dimethyl-10β-ergoline
Systematic IUPAC name
(6aR,9R,10aS)-7,9-Dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline
Other names
  • 6,8-Dimethylergoline
  • Costaclavine
  • Epicostaclavin
  • Festuclavin
  • Festuclavine
  • Pyroclavin
  • Pyroclavine[1]
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H20N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-5,8,10,13,15,17H,6-7,9H2,1-2H3/t10-,13+,15-/m1/s1
    Key: VLMZMRDOMOGGFA-RIEGTJTDSA-N
  • InChI=1/C16H20N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-5,8,10,13,15,17H,6-7,9H2,1-2H3/t10-,13+,15-/m1/s1
    Key: VLMZMRDOMOGGFA-RIEGTJTDBP
  • C[C@@H]1C[C@@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)C
Properties
C16H20N2
Molar mass 240.350 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Costaclavin is an ergoline fungal isolate, chemically related to festuclavine. It was first isolated from Agropyrum fungi in 1956[2] and its chemical structure was elucidated in 1976.[3]

Several laboratory syntheses of costaclavin have been reported.[4][5]

References

[edit]
  1. ^ "PubCHEM Open Chemistry Database". NCBI. Retrieved 2015-01-17.
  2. ^ Abe, Matazō; Yamatodani, Saburō; Yamano, Togō; Kusumoto, Mitsugi (1956). "Isolation of Two New Water-Soluble Alkaloids, Pyroclavine and Costaclavine". Bulletin of the Agricultural Chemical Society of Japan. 20: 59–60. doi:10.1080/03758397.1956.10857305.
  3. ^ Ninomiya, Ichiya; Kiguchi, Toshiko (1976). "New synthesis of clavine: Determination of the structure of costaclavine by nuclear magnetic resonance spectroscopy". Journal of the Chemical Society, Chemical Communications (16): 624. doi:10.1039/C39760000624.
  4. ^ Liu, Haichao; Zhang, Xiwu; Shan, Dong; Pitchakuntla, Mallesham; Ma, Yongfan; Jia, Yanxing (2017). "Total Syntheses of Festuclavine, Pyroclavine, Costaclavine, epi -Costaclavine, Pibocin A, 9-Deacetoxyfumigaclavine C, Fumigaclavine G, and Dihydrosetoclavine". Organic Letters. 19 (12): 3323–3326. doi:10.1021/acs.orglett.7b01504. PMID 28593757.
  5. ^ Osanai, Kumi; Yokoyama, Yuusaku; Kondo, Kazuhiro; Murakami, Yasuoki (1999). "Total Synthesis of Optically Active Costaclavine. Synthetic Studies of Indoles and Related Compounds. Part 48". Chemical and Pharmaceutical Bulletin. 47 (11): 1587–1590. doi:10.1248/cpb.47.1587.



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