Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol

Part of the Springer Theses book series (Springer Theses)


Enantioselective total synthesis of the biologically important indole alkaloids, (+)-lysergol, (+)-isolysergol and (+)-lysergic acid is described. Key features of these total synthesis include: (1) a facile synthesis of a chiral 1,3-amino alcohol via the Pd(0) and In(I)-mediated reductive coupling reaction between l-serine-derived 2-ethynylaziridine and formaldehyde; (2) the Cr(II)/Ni(0)-mediated Nozaki−Hiyama−Kishi (NHK) reaction of an indole-3-acetaldehyde with iodoalkyne; and (3) Pd(0)-catalyzed domino cyclization of an amino allene bearing a bromoindolyl group. This domino cyclization enabled direct construction of the C/D ring system of the ergot alkaloids skeleton as well as the creation of the C5 stereogenic center with transfer of the allenic axial chirality to the central chirality.


Ergot Alkaloid Flash Chromatography Oily Residue Saturated NaHCO3 Lysergic Acid 
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Copyright information

© Springer 2012

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

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