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Literature DB >> 19279674

Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Abstract

To unambiguously confirm the actual product in autoxidation of salvinorin A under basic conditions, deacetyl-1,10-didehydrosalvinorin G was synthesized from salvinorin C via intermediate salvinorin H. Furthermore, oxidation of salvinorin D with manganese dioxide gave salvinorin G in good yield.

Entities: Chemical

Year: 2008 PMID： 19279674 PMCID： PMC2390901 DOI： 10.1016/j.tetlet.2008.01.065

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

26 in total

1. Synthesis and in vitro pharmacological studies of new C(4)-modified salvinorin A analogues.

Authors: David Y W Lee; Minsheng He; Lee-Yuan Liu-Chen; Yulin Wang; Jian-Guo Li; Wei Xu; Zhongze Ma; William A Carlezon; Bruce Cohen
Journal: Bioorg Med Chem Lett Date: 2006-08-30 Impact factor: 2.823

2. Synthesis of salvinorin A analogues as opioid receptor probes.

Authors: Kevin Tidgewell; Wayne W Harding; Anthony Lozama; Howard Cobb; Kushal Shah; Pavitra Kannan; Christina M Dersch; Damon Parrish; Jeffrey R Deschamps; Richard B Rothman; Thomas E Prisinzano
Journal: J Nat Prod Date: 2006-06 Impact factor: 4.050

3. Autoxidation of salvinorin A under basic conditions.

Authors: Thomas A Munro; Glenn W Goetchius; Bryan L Roth; Timothy A Vortherms; Mark A Rizzacasa
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

4. New neoclerodane diterpenoids isolated from the leaves of Salvia divinorum and their binding affinities for human kappa opioid receptors.

Authors: David Y W Lee; Zhongze Ma; Lee-Yuan Liu-Chen; Yulin Wang; Yong Chen; William A Carlezon; Bruce Cohen
Journal: Bioorg Med Chem Date: 2005-10-01 Impact factor: 3.641

5. 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

6. Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum.

Authors: L J Valdés; H M Chang; D C Visger; M Koreeda
Journal: Org Lett Date: 2001-11-29 Impact factor: 6.005

7. Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues.

Authors: David Y W Lee; Minsheng He; Leelakrishna Kondaveti; Lee-Yuan Liu-Chen; Zhongze Ma; Yulin Wang; Yong Chen; Jian-Guo Li; Cecile Beguin; William A Carlezon; Bruce Cohen
Journal: Bioorg Med Chem Lett Date: 2005-10-01 Impact factor: 2.823

8. 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

9. 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

10. 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

2 in total

Review 1. 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

2. Novel neoclerodane diterpene derivatives from the smoke of salvinorin A.

Authors: Zhongze Ma; Gang Deng; David Y W Lee
Journal: Tetrahedron Lett Date: 2010-09-29 Impact factor: 2.415

2 in total