Literature DB >> 14703336

A new synthesis of lysergic acid.

James B Hendrickson1, Jian Wang.   

Abstract

[reaction: see text] (+/-)-Lysergic acid has been synthesized via an economical 8-step route from 4-bromoindole and isocinchomeronic acid without the need to protect the indole during the synthesis. Initial efforts to form the simpler 3-acylindole derivatives first and then cyclize these were unsuccessful in the cyclization step.

Entities:  

Year:  2004        PMID： 14703336     DOI： 10.1021/ol0354369

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


  7 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

2.  Total synthesis of (+)-lysergic acid.

Authors:  Rentaro Kanno; Satoshi Yokoshima; Motomu Kanai; Tohru Fukuyama
Journal:  J Antibiot (Tokyo)       Date:  2017-07-19       Impact factor: 2.649

3.  Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.

Authors:  Jason A Deck; Stephen F Martin
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  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.

Authors:  Markondaiah Bekkam; Huaping Mo; David E Nichols
Journal:  Org Lett       Date:  2011-12-16       Impact factor: 6.005

5.  2-(4-Bromo-1H-indol-3-yl)acetonitrile.

Authors:  Qiu-Xia Mao; Chen-Guang Zhang; Jin-Feng Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-18

6.  Reconstituting the complete biosynthesis of D-lysergic acid in yeast.

Authors:  Garrett Wong; Li Rong Lim; Yong Quan Tan; Maybelle Kho Go; David J Bell; Paul S Freemont; Wen Shan Yew
Journal:  Nat Commun       Date:  2022-02-07       Impact factor: 14.919

7.  Effects of N-oxidation on the molecular and crystal structures and properties of isocinchomeronic acid, its metal complexes and their supramolecular architectures: experimental, CSD survey, solution and theoretical approaches.

Authors:  Zahra Hosseini-Hashemi; Masoud Mirzaei; Ameneh Jafari; Peyman Hosseinpour; Mohammad Yousefi; Antonio Frontera; Mahmoud Lari Dashtbayaz; Mojtaba Shamsipur; Mehdi Ardalani
Journal:  RSC Adv       Date:  2019-08-14       Impact factor: 3.361
  7 in total

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