Chemo- and Diastereoselective Hydrosilylation of Amorphadiene toward the Synthesis of Artemisinin.

Geoffrey Schwertz, Andrea Zanetti, Marllon Nascimento de Oliveira, Mario Andrés Gomez Fernandez, Zacharias Amara, Janine Cossy

Open access · hybridAbstract read

PubMed Full text at PMC Publisher

In one paragraph

Article in The Journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing papers in PubMed

0.5field-weighted citation impact, top 40% of its field

1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed, 8 citations in OpenAlex.

Site-Selective Functionalization of Unactivated Allylic C-H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene.Organic letters · 2023
Article

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors at 2 institutions in 1 country.

Geoffrey SchwertzMolecular, Macromolecular Chemistry and Materials, ESPCI Paris/CNRS/PSL Research University, 10 rue Vauquelin, 75231 Paris cedex 05, France.

Andrea ZanettiMolecular, Macromolecular Chemistry and Materials, ESPCI Paris/CNRS/PSL Research University, 10 rue Vauquelin, 75231 Paris cedex 05, France.

Marllon Nascimento de OliveiraEquipe de Chimie Moléculaire, Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire (GBCM), EA 7528, Conservatoire national des arts et métiers, HESAM Université, 2 rue Conté, 75003 Paris cedex 03, France.

Mario Andrés Gomez FernandezEquipe de Chimie Moléculaire, Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire (GBCM), EA 7528, Conservatoire national des arts et métiers, HESAM Université, 2 rue Conté, 75003 Paris cedex 03, France.

Zacharias AmaraEquipe de Chimie Moléculaire, Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire (GBCM), EA 7528, Conservatoire national des arts et métiers, HESAM Université, 2 rue Conté, 75003 Paris cedex 03, France.ORCID 0000-0001-6824-1116

Janine CossyMolecular, Macromolecular Chemistry and Materials, ESPCI Paris/CNRS/PSL Research University, 10 rue Vauquelin, 75231 Paris cedex 05, France.ORCID 0000-0001-8746-9239

Centre National de la Recherche Scientifique · FRLaboratoire de Chimie Moléculaire · FR

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A formal synthesis of artemisinin starting from amorphadiene is described. This new route relies on the development of a catalytic chemo- and diastereoselective hydrosilylation. The practicability of this method is demonstrated by converting amorphadiene to dihydroartemisinic aldehyde using a one-pot hydrosilylation/oxidation sequence, minimizing the number of purifications and maximizing the productivity through a practical one-pot procedure. In addition, this approach can be coupled with a crystallization-induced diastereoselective transformation (CIDT) to enhance the optical purity of the key target intermediate, dihydroartemisinic aldehyde.

Indexed as

ArtemisininsPolycyclic Sesquiterpenesamorpha-4,11-dieneArtemisininsPolycyclic Sesquiterpenes

Identifiers

PMID32643937

DOI10.1021/acs.joc.0c00617

PMCPMC7418106

OpenAlexW3041202429

What OpenQuestion holds

Textmetadata

Read underepoch 390

Registered trials

None linked

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.