Literature DB >> 16292839

Autoxidation of salvinorin A under basic conditions.

Thomas A Munro1, Glenn W Goetchius, Bryan L Roth, Timothy A Vortherms, Mark A Rizzacasa.   

Abstract

[reaction: see text] Treatment of salvinorin A (1a) with KOH in MeOH gave the enedione 3, for which the dienone structure 7 was recently proposed. Also isolated, after methylation, were the secotriesters 4a-c. A mechanism for this unusual series of autoxidations is proposed. Surprisingly, 4a showed weak affinity at the kappa-opioid receptor. Divinatorins A-C (2a-c) showed no affinity at opioid receptors. Attempted reduction of 3 to a novel salvinorin diol (9d) was unsuccessful, but careful deacetylation of salvinorin C (9a) provided a viable route to this compound. A general method for identifying salvinorin 8-epimers by TLC is also presented.

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Year:  2005        PMID： 16292839      PMCID： PMC2778035          DOI： 10.1021/jo051813e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

1.  Divinatorins A-C, new neoclerodane diterpenoids from the controlled sage Salvia divinorum.

Authors:  Andrea K Bigham; Thomas A Munro; Mark A Rizzacasa; Roy M Robins-Browne
Journal:  J Nat Prod       Date:  2003-09       Impact factor: 4.050

2.  Studies toward the pharmacophore of salvinorin A, a potent kappa opioid receptor agonist.

Authors:  Thomas A Munro; Mark A Rizzacasa; Bryan L Roth; Beth A Toth; Feng Yan
Journal:  J Med Chem       Date:  2005-01-27       Impact factor: 7.446

3.  Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to kappa-opioid receptors.

Authors:  Feng Yan; Philip D Mosier; Richard B Westkaemper; Jeremy Stewart; Jordan K Zjawiony; Timothy A Vortherms; Douglas J Sheffler; Bryan L Roth
Journal:  Biochemistry       Date:  2005-06-21       Impact factor: 3.162

4.  Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2).

Authors:  Cécile Béguin; Michele R Richards; Yulin Wang; Yong Chen; Lee-Yuan Liu-Chen; Zhongze Ma; David Y W Lee; William A Carlezon; Bruce M Cohen
Journal:  Bioorg Med Chem Lett       Date:  2005-06-02       Impact factor: 2.823

5.  Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum.

Authors:  Wayne W Harding; Kevin Tidgewell; Matthew Schmidt; Kushal Shah; Christina M Dersch; John Snyder; Damon Parrish; Jeffrey R Deschamps; Richard B Rothman; Thomas E Prisinzano
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

6.  A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A.

Authors:  Kevin Tidgewell; Wayne W Harding; Mark Schmidt; Kenneth G Holden; Daryl J Murry; Thomas E Prisinzano
Journal:  Bioorg Med Chem Lett       Date:  2004-10-18       Impact factor: 2.823

7.  Salvinorins D-F, new neoclerodane diterpenoids from Salvia divinorum, and an improved method for the isolation of salvinorin A.

Authors:  Thomas A Munro; Mark A Rizzacasa
Journal:  J Nat Prod       Date:  2003-05       Impact factor: 4.050

8.  Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations.

Authors:  Charles Chavkin; Sumit Sud; Wenzhen Jin; Jeremy Stewart; Jordan K Zjawiony; Daniel J Siebert; Beth Ann Toth; Sandra J Hufeisen; Bryan L Roth
Journal:  J Pharmacol Exp Ther       Date:  2004-01-08       Impact factor: 4.030

9.  Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist.

Authors:  Bryan L Roth; Karen Baner; Richard Westkaemper; Daniel Siebert; Kenner C Rice; SeAnna Steinberg; Paul Ernsberger; Richard B Rothman
Journal:  Proc Natl Acad Sci U S A       Date:  2002-08-21       Impact factor: 11.205

10.  Salvia divinorum and salvinorin A: new pharmacologic findings.

Authors:  D J Siebert
Journal:  J Ethnopharmacol       Date:  1994-06       Impact factor: 4.360
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  7 in total

Review 1.  Salvinorin A analogs as probes in opioid pharmacology.

Authors:  Thomas E Prisinzano; Richard B Rothman
Journal:  Chem Rev       Date:  2008-05       Impact factor: 60.622

Review 2.  Neoclerodanes as atypical opioid receptor ligands.

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

Review 3.  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

4.  Revised structure of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2007-07-30       Impact factor: 2.415

5.  Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Authors:  Zhongze Ma; David Y W Lee
Journal:  Tetrahedron Lett       Date:  2008-03-10       Impact factor: 2.415

Review 6.  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

7.  8-epi-Salvinorin B: crystal structure and affinity at the kappa opioid receptor.

Authors:  Thomas A Munro; Katharine K Duncan; Richard J Staples; Wei Xu; Lee-Yuan Liu-Chen; Cécile Béguin; William A Carlezon; Bruce M Cohen
Journal:  Beilstein J Org Chem       Date:  2007-01-09       Impact factor: 2.883
  7 in total

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