Evidence map›Paper›PMID 24490808›Full record

ArticleOrganic letters2013

Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

Barry M Trost, David J Michaelis, Sushant Malhotra

Abstract read
In one paragraph

Article in Organic letters, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
–field-weighted citation impact
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

4 citing papers in PubMed.

  1. Review
  2. Article
  3. Review
  4. 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

3 authors.

Barry M TrostDepartment of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
David J Michaelis
Sushant Malhotra

Funding

NOVEL SYNTHETIC APPROACHES TO ANTITUMOR COMPOUNDSR01GM033049 · NIGMS · UNIVERSITY OF WISCONSIN MADISON · PI TROST, BARRY M · 1985 to 2016
$6.5M
Total Synthesis of Cytotoxic ent-Kauranoid Natural ProductsF32GM093467 · NIGMS · STANFORD UNIVERSITY · PI MICHAELIS, DAVID JOHN · 2010 to 2012
$146k
NIGMS NIH HHS F32 GM093467NIGMS NIH HHS GM033049NIGMS NIH HHS R01 GM033049
6 · The paper itself

Abstract

A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ethyl stereocenter.

Indexed as

Biological ProductsBridged Bicyclo Compounds, HeterocyclicLactonesMolecular ConformationStereoisomerismBiological ProductsBridged Bicyclo Compounds, HeterocyclicLactonespeloruside A

Identifiers

PMID24490808
PMCPMC3939827

What OpenQuestion holds

Textmetadata
LicenceTDM
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.