Easy access to a cyclic key intermediate for the synthesis of trisporic acids and related compounds.

José A González-Delgado, Gustavo Escobar, Jesús F Arteaga, Alejandro F Barrero

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing 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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

4 authors.

José A González-DelgadoDepartment of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain.

Gustavo EscobarDepartment of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain.

Jesús F ArteagaCIQSO-Center for Research in Sustainable Chemistry and Department of Chemical Engineering, Physical Chemistry and Organic Chemistry, University of Huelva, Avda 3 Marzo s/n, 21071 Huelva, Spain. jesus.fernandez@diq.uhu.es.

Alejandro F BarreroDepartment of Organic Chemistry and Institute of Biotechnology, University of Granada, Avda Fuentenueva s/n, 18071 Granada, Spain. afbarre@ugr.es.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C-3, C-8 and C-9, and a D1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.

Indexed as

CarbonCatalysisCyclizationCyclohexanesEpoxy CompoundsFatty Acids, UnsaturatedMolecular StructureStereoisomerismCarbonCyclohexaneCyclohexanesEpoxy CompoundsFatty Acids, Unsaturatedtrisporic acid

Identifiers

PMID24496268

DOI10.3390/molecules19021748

PMCPMC6271007

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.