Evidence map›Paper›PMID 29863356›Full record

ArticleOrganic letters2018

Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Alyssa H Antropow, Nicholas R Garcia, Kolby L White, Mohammad Movassaghi

Abstract read
In one paragraph

Article in Organic letters, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Review
  3. Article
  4. Article
  5. Total Syntheses of DihydroindoleOrganic letters · 2020
    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.

Alyssa H AntropowDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
Nicholas R GarciaDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
Kolby L WhiteDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
Mohammad MovassaghiDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.ORCID 0000-0003-3080-1063

Funding

Synthesis and Study of Complex Natural ProductsR01GM074825 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI MOVASSAGHI, MOHAMMAD · 2005 to 2019
$4.6M
NIGMS NIH HHS R01 GM074825
6 · The paper itself

Abstract

The first enantioselective total synthesis of (-)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (-)-vallesine, from a common intermediate.

Indexed as

AlkaloidsBoron CompoundsCyclizationIndolesMolecular StructureOxidation-ReductionStereoisomerismAlkaloidsBoron CompoundsIndoles

Identifiers

PMID29863356
PMCPMC6021010

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.