Evidence map›Paper›PMID 26561788›Full record

ArticleOrganic letters2015

A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)-C(9) Fragment of the Epothilones.

Corinne N Foley, James L Leighton

Abstract read
In one paragraph

Article in Organic letters, 2015. 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
–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

2 citing papers in PubMed.

  1. Article
  2. 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

2 authors.

Corinne N FoleyDepartment of Chemistry, Columbia University , 3000 Broadway, New York, New York 10027, United States.
James L LeightonDepartment of Chemistry, Columbia University , 3000 Broadway, New York, New York 10027, United States.

Funding

Asymmetric Synthesis of Marcolide AntibioticsR01GM058133 · NIGMS · COLUMBIA UNIV NEW YORK MORNINGSIDE · PI LEIGHTON, JAMES L · 1998 to 2017
$4.7M
NIGMS NIH HHS R01 GM058133NIGMS NIH HHS R01GM058133
6 · The paper itself

Abstract

A second-generation synthesis of the C(1)-C(9) fragment of the epothilones is reported. The key tandem intramolecular silylformylation/crotylsilylation/"aprotic" Tamao oxidation sequence has been redeveloped as a stepwise intermolecular variant, allowing excellent levels of diastereoselectivity in the crotylation step and proceeds in 50% overall yield on gram scale. An improved synthesis of the homopropargyl alcohol starting material is also described, which proceeds in four steps and >99% ee from inexpensive starting materials and is amenable to multigram scales.

Indexed as

AlcoholsEpothilonesMolecular StructureOxidation-ReductionStereoisomerismAlcoholsEpothilones

Identifiers

PMID26561788
PMCPMC4811194

What OpenQuestion holds

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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.