Literature DB >> 22176338

A reported "new synthesis of lysergic acid" yields only the derailment product: methyl 5-methoxy-4,5-dihydroindolo[4,3-f,g]quinoline-9-carboxylate.

Markondaiah Bekkam1, Huaping Mo, David E Nichols.   

Abstract

The treatment of ethyl 6-formyl-5-(1H-indol-4-yl)pyridine-3-carboxylate (2) with NaOMe or NaOH in methanol solution at room temperature under the reported reaction conditions afforded solely product 4 in 80% yield, rather than anticipated product 3.
© 2011 American Chemical Society

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Year:  2011        PMID： 22176338      PMCID： PMC3265357          DOI： 10.1021/ol203048q

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists.

Authors:  J J Chambers; D M Kurrasch-Orbaugh; M A Parker; D E Nichols
Journal:  J Med Chem       Date:  2001-03-15       Impact factor: 7.446

2.  Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes.

Authors:  A P Monte; D Marona-Lewicka; A Kanthasamy; E Sanders-Bush; D E Nichols
Journal:  J Med Chem       Date:  1995-03-17       Impact factor: 7.446

3.  Stereoselective LSD-like activity in d-lysergic acid amides of (R)- and (S)-2-aminobutane.

Authors:  R Oberlender; R C Pfaff; M P Johnson; X M Huang; D E Nichols
Journal:  J Med Chem       Date:  1992-01-24       Impact factor: 7.446

4.  A new synthesis of lysergic acid.

Authors:  James B Hendrickson; Jian Wang
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

5.  Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD).

Authors:  David E Nichols; Stewart Frescas; Danuta Marona-Lewicka; Deborah M Kurrasch-Orbaugh
Journal:  J Med Chem       Date:  2002-09-12       Impact factor: 7.446

6.  Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.

Authors:  A P Monte; D Marona-Lewicka; N V Cozzi; D E Nichols
Journal:  J Med Chem       Date:  1993-11-12       Impact factor: 7.446
  6 in total
  1 in total

1.  Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

Authors:  Kiyoun Lee; Yam B Poudel; Christopher M Glinkerman; Dale L Boger
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457
  1 in total

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