ArticleJournal of the American Chemical Society2022
Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
5 citing papers in PubMed.
- Directed Heterodimerization: Total Synthesis of (-)-Folicangine, (-)-Voafolidine, (-)-Isovoafolidine, and (-)-Tabernaesine B.Organic letters · 2026Article
- Total Synthesis of the Spirocyclic Bis-Indole Alkaloid (-)-Owerreine via a [4+2] Annulation.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of (-)-Owerreine and (-)-Anhydrovobtusine.Organic letters · 2025Article
- Total Synthesis of (+)-Hazuntiphylline, (-)-Anhydrohazuntiphyllidine, and (-)-Hazuntiphyllidine.Journal of the American Chemical Society · 2025Article
- Development of a Non-Directed Petasis-Type Reaction by an Aromaticity-Disrupting Strategy.Angewandte Chemie (International ed. in English) · 2023Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
Abstract
We describe the first total synthesis of complex aspidosperma alkaloids (-)-voacinol and (-)-voacandimine C via a late-stage C7-methylenation strategy inspired by a biogenetic hypothesis. We envisioned rapid access to these natural alkaloids from a common, symmetrical precursor assembled by methylenation of a D-ring-oxidized variant of the structurally related natural product (-)-deoxoapodine. Chemoselective N9-oxidation of a pentacyclic deoxoapodine precursor enabled the synthesis of the corresponding hexacyclic C8-aminonitrile. Stereocontrolled methylenation of a C8-enamine derivative of deoxoapodine, accessed by ionization of the C8-aminonitrile, afforded a symmetrical dodecacyclic bisaminonitrile as a versatile precursor to these bisindole alkaloids. The final-stage, biosynthesis-inspired, controlled reductive opening of the oxolane substructures of this dodecacyclic intermediate provided a unified approach to (-)-voacinol and (-)-voacandimine C, while direct reduction of the same intermediate afforded the structurally related (-)-methylenebisdeoxoapodine.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.