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Organic letters

ISSN 1523-7052

4 papers in the library · 213 citations · publishing 2001-2024

Papers

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

Organic letters November 29, 2001 L J Valdés, H M Chang, D C Visger et al. 81 citations

A minor compound called salvinorin C was isolated from the leaves of the Mexican mint Salvia divinorum. Its chemical structure was determined using detailed proton and carbon-13 nuclear magnetic resonance (NMR) experiments, along with comparisons to the NMR data of three acetate derivatives made from the major reduction product of salvinorin A. This work adds to the understanding of the chemical constituents of this psychoactive plant.

Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.

Organic letters May 20, 2016 Gaoyuan Zhao, Xingang Xie, Haiyu Sun et al. 64 citations

A bioinspired collective synthesis strategy enabled the total syntheses of seven iboga-type indole alkaloids: tabertinggine, ibogamine, ibogaine, ibogaine hydroxyindolenine, 3-oxoibogaine hydroxyindolenine, iboluteine, and ervaoffines D. Tabertinggine and its congeners act as precursors for biomimetic transformations into other iboga-type alkaloids.

Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A.

Organic letters April 3, 2008 Masato Nozawa, Yuhki Suka, Takashi Hoshi et al. 63 citations

A potent hallucinogen, Salvinorin A, recognized for its unique effects on the brain, has been successfully created in the lab. Scientists achieved its total synthesis in 20 precise steps, starting from a foundational chemical compound. This significant accomplishment offers a controlled method to produce this intricate molecule, enabling deeper understanding and diverse applications.

Solving a Mystery with Classical and Dual Photoredox Catalysis: Application of Nickel in the Synthesis of Ergot Alkaloids.

Organic letters May 24, 2024 Jan Brauer, Rainer Wiechert, Anika Hahn et al. 5 citations

A new synthetic route to the ergot alkaloid lysergene and a formal total synthesis of LSD avoids palladium, using two nickel-catalyzed steps instead. A key intermediate previously reported by Hendrickson et al. in 2004 could not be reproduced with matching spectral data, raising doubts about their original route. However, the authors successfully leveraged this elusive intermediate to complete their own synthesis.