Research published in Tetrahedron Letters - The Consciousness Library

Synthetic studies toward the marine alkaloid convolutindole A, a structurally remarkable derivative of the hallucinogen N,N-Dimethyltryptamine (DMT)

Tetrahedron Letters September 13, 2023 Karen Ichikawa, Jessica C. Neville, Yihan Yu et al. 3 citations

Herein we report the results of a synthetic strategy toward the marine alkaloid convolutindole A, a structurally remarkable derivative of the hallucinogen N,N-dimethyltryptamine (DMT). While attempts to forge an advanced tryptamine intermediate using the Fischer reaction were unsuccessful, an iterative C-H functionalisation strategy proved more fruitful. Subjecting 6-bromoindole to an...

DOI: 10.1016/j.tetlet.2023.154756

Novel neoclerodane diterpene derivatives from the smoke of salvinorin A.

Tetrahedron Letters September 29, 2010 Zhongze Ma, Gang Deng, David Y W Lee 11 citations

Salvinorin A is a naturally-occurring potent and selective kappa opioid receptor agonist, and smoking salvinorin A produces the most intense hallucinogenic effects in human. Eight neoclerodane diterpene derivatives were isolated from the smoke of salvinorin A, and their structures were identified by spectroscopic methods. The major structural changes include epimerizations, eliminations, and...

DOI: 10.1016/j.tetlet.2010.07.144 Full text Salvinorin a Salvia divinorum Hallucinogen Psychoactive substance +13

Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Tetrahedron Letters March 10, 2008 Zhongze Ma, David Y W Lee

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.

DOI: 10.1016/j.tetlet.2008.01.065 Full text

Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure.

Tetrahedron Letters February 4, 2008 Ruslan V Bikbulatov, Jeremy Stewart, Wentao Jin et al.

Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the κ-opioid receptor (KOR), were obtained in good yields. The derivatives are remarkable for their unusual and unique hemiacetal structure in the salvinorin series of compounds. The formation of the hemiacetal occurs with epimerization at C-12, thus preserving the original...

DOI: 10.1016/j.tetlet.2007.12.041 Full text

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

Tetrahedron Letters July 30, 2007 Zhongze Ma, David Y W Lee

In comparison with the NMR data of salvinorin A and its 8-epimer, the published structure of deacetyl-1,10-didehydrosalvinorin G was revised to its 8-epimer. The stereochemistry of 8-epi-deacetyl-1,10-didehydrosalvinorin G was further confirmed by NOESY and chemical synthesis.

DOI: 10.1016/j.tetlet.2007.05.179 Full text

Papers

Synthetic studies toward the marine alkaloid convolutindole A, a structurally remarkable derivative of the hallucinogen N,N-Dimethyltryptamine (DMT)

Novel neoclerodane diterpene derivatives from the smoke of salvinorin A.

Synthesis of deacetyl-1,10-didehydrosalvinorin G.

Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure.

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