Literature DB >> 18311991

Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A.

Masato Nozawa1, Yuhki Suka, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara.   

Abstract

Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective kappa-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.

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Year:  2008        PMID: 18311991     DOI: 10.1021/ol800101v

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


  14 in total

Review 1.  Natural Products in the "Marketplace": Interfacing Synthesis and Biology.

Authors:  Benjamin J Huffman; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2019-02-13       Impact factor: 15.419

Review 2.  Neoclerodanes as atypical opioid receptor ligands.

Authors:  Thomas E Prisinzano
Journal:  J Med Chem       Date:  2013-04-18       Impact factor: 7.446

3.  Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.

Authors:  Alexander M Sherwood; Samuel E Williamson; Rachel S Crowley; Logan M Abbott; Victor W Day; Thomas E Prisinzano
Journal:  Org Lett       Date:  2017-09-14       Impact factor: 6.005

Review 4.  Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A.

Authors:  Christopher W Cunningham; Richard B Rothman; Thomas E Prisinzano
Journal:  Pharmacol Rev       Date:  2011-03-28       Impact factor: 25.468

Review 5.  A review of salvinorin analogs and their kappa-opioid receptor activity.

Authors:  Jeremy J Roach; Ryan A Shenvi
Journal:  Bioorg Med Chem Lett       Date:  2018-03-12       Impact factor: 2.823

6.  Modification of the furan ring of salvinorin A: identification of a selective partial agonist at the kappa opioid receptor.

Authors:  Cécile Béguin; Katharine K Duncan; Thomas A Munro; Douglas M Ho; Wei Xu; Lee-Yuan Liu-Chen; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem       Date:  2008-12-14       Impact factor: 3.641

Review 7.  Natural products as tools for neuroscience: discovery and development of novel agents to treat drug abuse.

Authors:  Thomas E Prisinzano
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

Review 8.  Chemical syntheses of the salvinorin chemotype of KOR agonist.

Authors:  Sarah J Hill; Aurélien U C M Brion; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2020-11-18       Impact factor: 13.423

Review 9.  Chemical methods for the synthesis and modification of neoclerodane diterpenes.

Authors:  Anthony Lozama; Thomas E Prisinzano
Journal:  Bioorg Med Chem Lett       Date:  2009-07-17       Impact factor: 2.823

Review 10.  Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

Authors:  Soumen Chakraborty; Susruta Majumdar
Journal:  Biochemistry       Date:  2020-09-22       Impact factor: 3.162

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