Evidence map›Paper›PMID 36592432›Full record

ArticleOrganic letters2023

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

Nicholas A Clanton, Nicolas A Wilson, Eliezer Ortiz, Shawn T Blumberg, Doug E Frantz

Open access · hybridAbstract read
In one paragraph

Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
1.5field-weighted citation impact, top 20% 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

2 citing papers in PubMed, 6 citations in OpenAlex.

  1. Review
  2. Review
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

5 authors at 2 institutions in 1 country.

Nicholas A ClantonThe Max and Minnie Tomerlin Voelcker Laboratory for Organic Chemistry, Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.ORCID 0000-0001-5936-4878
Nicolas A WilsonThe Max and Minnie Tomerlin Voelcker Laboratory for Organic Chemistry, Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.
Eliezer OrtizThe Max and Minnie Tomerlin Voelcker Laboratory for Organic Chemistry, Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.ORCID 0000-0002-7349-6081
Shawn T BlumbergDepartment of Pharmaceuticals & Bioengineering, Southwest Research Institute, San Antonio, Texas 78238, United States.
Doug E FrantzThe Max and Minnie Tomerlin Voelcker Laboratory for Organic Chemistry, Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.ORCID 0000-0002-4509-4579
The University of Texas at San Antonio · USSouthwest Research Institute · US

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The site-selective functionalization of unactivated allylic C-H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is shown with further extrapolation to the first large-scale telescoped chemical synthesis of artemisinic acid from amorphadiene. Finally, application of the method for the successful site-selective functionalization of unactivated allylic C-H bonds in other terpene-based natural products is also highlighted.

Indexed as

ArtemisininsPolycyclic Sesquiterpenesamorpha-4,11-dieneartemisininArtemisininsPolycyclic Sesquiterpenes

Identifiers

PMID36592432
PMCPMC9841608
OpenAlexW4313454265

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.