Organic Letters
May 24, 2024
Jan Brauer, Rainer Wiechert, Anika Hahn et al.
5 citations
A short synthesis of the ergot alkaloid lysergene and a formal total synthesis of lysergic acid diethylamide (LSD) under the avoidance of palladium and including two nickel-catalyzed steps instead have been developed. A key intermediate of this approach has already been reported by Hendrickson et al. in 2004 (Hendrickson, J.B. et al. Org. Lett. 2004, 6, 3-5), yet the spectral data do not match,...
Organic Letters
May 20, 2016
Gaoyuan Zhao, Xingang Xie, Haiyu Sun et al.
64 citations
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic...
Organic Letters
April 3, 2008
Masato Nozawa, Yuhki Suka, Takashi Hoshi et al.
63 citations
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.
Organic Letters
March 22, 2003
Kateri A. Ahrendt, Robert G. Bergman, Jonathan A. Ellman
99 citations
[reaction: see text] A tetrahydrobis(benzofuran) mescaline analogue has been prepared in six steps and 38% overall yield from (4'-O-methyl)methyl gallate. The key step in this synthesis is a tandem cyclization reaction via directed C[bond]H activation followed by olefin insertion.
Organic Letters
November 29, 2001
Leander J. Valdés, H M Chang, Daniel C. Visger et al.
81 citations
Salvinorin C (1), a minor component from a biologically active TLC fraction, was isolated from the leaves of the Mexican mint Salvia divinorum. Its structure was elucidated on the basis of extensive proton and C-13 NMR experiments, as well as by comparison of the NMR data with those of the mono- and diacetate derivatives 5-7 of the major NaBH(4)-reduction product of salvinorin A (2)....