Costaclavin

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
CAS Number	436-41-9  Y
3D model (JSmol)	Interactive image
ChemSpider	141006
PubChem CID	160462
UNII	GLS7Y869AV  Y
CompTox Dashboard (EPA)	DTXSID90963054
InChI 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
SMILES C[C@@H]1C[C@@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)C
Properties
Chemical formula	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). Infobox references

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

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.