Horsfiline Explained

Horsfiline is an oxindole alkaloid found in the plant Horsfieldia superba,^[1] which is used in traditional herbal medicine. It has analgesic effects and has been the subject of research both to produce it synthetically by convenient routes^{[2] [3] [4] [5] [6] [7] [8]} and to develop analogues and derivatives which may have improved analgesic effects.^{[9] [10]}

It is a member of the spiroindolone class. Elacomine has a similar chemical structure.

Notes and References

1. Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B . 1991 . An oxindole alkaloid from Horsfieldia superba . Journal of Organic Chemistry . 56 . 23. 6527–6530 . 10.1021/jo00023a016 .
2. Lakshmaiah G, Kawabata T, Shang M, Fuji K . Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination . The Journal of Organic Chemistry . 64 . 5 . 1699–1704 . March 1999 . 11674239 . 10.1021/jo981577q .
3. Cravotto G, Giovenzana GB, Pilati T, Sisti M, Palmisano G . Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline . The Journal of Organic Chemistry . 66 . 25 . 8447–53 . December 2001 . 11735524 . 10.1021/jo015854w .
4. Murphy JA, Tripoli R, Khan TA, Mali UW . Novel phosphorus radical-based routes to horsfiline . Organic Letters . 7 . 15 . 3287–9 . July 2005 . 16018642 . 10.1021/ol051095i .
5. Trost BM, Brennan MK . Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline . Organic Letters . 8 . 10 . 2027–30 . May 2006 . 16671773 . 2565574 . 10.1021/ol060298j .
6. Hong S, Jung M, Park Y, Ha MW, Park C, Lee M, Park HG . Efficient enantioselective total synthesis of (-)-horsfiline . . 19 . 29 . 9599–605 . July 2013 . 23836402 . 10.1002/chem.201301008 .
7. Mukaiyama T, Ogata K, Sato I, Hayashi Y . Asymmetric organocatalyzed Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde and the three one-pot sequential synthesis of (-)-horsfiline and (-)-coerulescine . . 20 . 42 . 13583–8 . October 2014 . 25155110 . 10.1002/chem.201403932 .
8. Buev EM, Moshkin VS, Sosnovskikh VY . Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids . . 82 . 23 . 12827–12833 . December 2017 . 29048900 . 10.1021/acs.joc.7b02193 .
9. Tsai YC, Liou JP, Liao R, Cheng CY, Tao PL . C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: a conformation-activity study . Bioorganic & Medicinal Chemistry Letters . 8 . 14 . 1813–8 . July 1998 . 9873439 . 10.1016/S0960-894X(98)00318-7 .
10. https://patents.google.com/patent/US6774132 Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132