- Synthesis of (+)-Lysergol and Its Analogues to Assess Serotonin Receptor Activity
-
An efficient synthesis of ergot alkaloid lysergol and its analogues is described, providing compounds for functional evaluation at the human 5-HT1A, 5-HT2A, 5-HT2B, or 5-HT2C receptors. Key features of the synthesis include the development of a tandem reaction to construct the multifunctionalized piperidine skeleton and use of a rhodium-catalyzed [3 + 2] annulation in the late-stage indole formation.
- Yuan, Haosen,Guo, Zhixian,Luo, Tuoping
-
-
Read Online
- Conversion of agroclavine to lysergol
-
The conversion of agroclavine (1) to lysergol (4) has been achieved in three steps utilising the dehydration of setoclavine (2) to lysergene (3).
- Harris,Horwell
-
-
Read Online
- Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction
-
A catalytic enantioselective construction of vicinal stereocenters is reported. The reaction takes advantage of thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester to afford exceptional levels of enantioselectivity (up to 97 % ee) with moderate diastereoselectivity (up to 4:1). Using this method, a cross-conjugated ester was synthesized in few steps, from which a 6-endo-trig cyclisation led to the formation of all required functionalities for total syntheses of ergot alkaloids. The strategy not only offers first total syntheses of ergot alkaloids, festuclavine (1 c), and pyroclavine (1 e), and but also an efficient and general approach to other congeners such as, lysergol (1 b), and isolysergol (1 d).
- Bhunia, Subhajit,Chaudhuri, Saikat,Bisai, Alakesh
-
supporting information
p. 11234 - 11238
(2017/08/26)
-
- Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups
-
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 allene bearing amino and bromoindolyl groups. 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.
- Inuki, Shinsuke,Iwata, Akira,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
-
experimental part
p. 2072 - 2083
(2011/05/12)
-
- Total synthesis of (±)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group
-
(Chemical Equation Presented) 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.
- Inuki, Shinsuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
-
supporting information; experimental part
p. 5239 - 5242
(2009/06/06)
-
- Dehydrogenation with Benzeneseleninic Anhydride in the Total Synthesis of Ergot Alkaloids
-
Investigation of the dehydrogenative conversion of indolines into indoles with benzeneseleninic anhydride (1) resulted in the development of an efficient standardised procedure, which was successfully applied to the final steps in first total synthesis of (+/-)-lysergol (18), (+/-)-isolysergol (27), and (+/-)-elymoclavine (29).
- Ninomiya, Ichiya,Hashimoto, Chiyomi,Kiguchi, Toshiko,Naito, Takeaki,Barton, Derek, H. R.,et al.
-
p. 707 - 713
(2007/10/02)
-
- A TOTAL SYNTHESIS OF (+/-)-LYSERGOL, A 9-ERGOLENE TYPE OF ERGOT ALKALOID
-
According to the synthetic route established on the despyrrole analog of the alkaloid, the first total synthesis of (+/-)-lysergol was completed.
- Kiguchi, Toshiko,Hashimoto, Chiyomi,Ninomiya, Ichiya
-
p. 1377 - 1380
(2007/10/02)
-
- TOTAL SYNTHESIS OF ERGOT ALKALOIDS, (+/-)-ELYMOCLAVINE AND (+/-)-ISOLYSERGOL
-
Two of the hitherto untouched ergot alkaloids, (+/-)-elymoclavine and (+/-)-isolysergol, were synthesized according to the synthetic route involving enamide photocyclization.
- Ninomiya, Ichiya,Hashimoto, Chiyomi,Kiguchi, Toshiko
-
p. 1035 - 1038
(2007/10/02)
-
