Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group
- 28 October 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (22), 5239-5242
- https://doi.org/10.1021/ol8022648
Abstract
Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (±)-lysergic acid, (±)-lysergol, and (±)-isolysergol was achieved.Keywords
This publication has 41 references indexed in Scilit:
- Recent synthetic studies on the ergot alkaloids and related compoundsThe Alkaloids: Chemistry and Biology, 2000
- A new synthesis of (.+-.)-lysergic acid.CHEMICAL & PHARMACEUTICAL BULLETIN, 1986
- A new synthesis of lysergic acidTetrahedron Letters, 1983
- A New Synthesis of (±)-Lysergic AcidHETEROCYCLES, 1982
- Total Synthesis of (±)‐Lysergic Acid by an Intramolecular Imino‐Diels‐Alder Reaction. Preliminary communicationHelvetica Chimica Acta, 1981
- A new synthetic route to (±)-lysergie acidTetrahedron Letters, 1976
- Une nouvelle synthese de l'acide lysergiqueTetrahedron Letters, 1969
- The Total Synthesis of Lysergic AcidJournal of the American Chemical Society, 1956
- Über die Isomerie von Lysergsäure und Isolysergsäure. 14. Mitteilung über MutterkornalkaloideHelvetica Chimica Acta, 1949
- THE ERGOT ALKALOIDSPublished by Elsevier BV ,1934