Evidence map›Paper›PMID 27300267›Full record

ArticleOrganic letters2016

Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Soma Maitra, Mahipal Bodugam, Salim Javed, Paul R Hanson

Abstract read
In one paragraph

Article in Organic letters, 2016. 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. Article
  2. Review
  3. Article
  4. P-Tether-Mediated, Iterative SOrganic letters · 2017
    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

4 authors.

Soma MaitraDepartment of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
Mahipal BodugamDepartment of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
Salim JavedDepartment of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
Paul R HansonDepartment of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.

Funding

Mentoring CoreP20GM103418 · NIGMS · UNIVERSITY OF KANSAS MEDICAL CENTER · PI SUSAN J. BROWN · 2012 to 2026
$63.0M
Methods for Bioactive Compound SynthesisR01GM077309 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI HANSON, PAUL R. · 2007 to 2016
$2.4M
Avance II 500 High Performance Digital NMR Spectrometer SystemS10RR024664 · NCRR · UNIVERSITY OF KANSAS LAWRENCE · PI VANDERVELDE, DAVID G · 2007 to 2007
$468k
AVIII HD 400 NMR spectrometer to replace existing DRX 400S10OD016360 · OD · UNIVERSITY OF KANSAS LAWRENCE · PI DOUGLAS, JUSTIN TRIGALET · 2014 to 2014
$297k
NCRR NIH HHS S10 RR024664NIGMS NIH HHS P20 GM103418NIGMS NIH HHS R01 GM077309NIH HHS S10 OD016360
6 · The paper itself

Abstract

The synthesis of the C9-C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki-Miyaura coupling reaction and a late-stage, one-pot sequential deprotection/cascade Achmatowicz rearrangement-spiroketalization to install the key spirocyclic intermediate present in the C9-C25 fragment of spirastrellolide B. The synthesis of the C9-C16 fragment 6 was accomplished via a phosphate tether mediated ring-closing metathesis (RCM), a subsequent hydroboration-oxidation protocol, followed by other stereoselective transformations in a facile manner. The spirocyclic intermediate was further functionalized utilizing a Lindlar/NaBH4 reduction protocol to furnish the C9-C25 subunit 3.

Indexed as

CyclizationMacrolidesMolecular StructureOxidation-ReductionSpiro CompoundsStereoisomerismMacrolidesspirastrellolide BSpiro Compounds

Identifiers

PMID27300267
PMCPMC4943334

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.