Evidence map›Paper›PMID 26130270›Full record

ArticleAngewandte Chemie (International ed. in English)2015

10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.

Jeffrey J Jackson, Hiroyuki Kobayashi, Sophia D Steffens, Armen Zakarian

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Total Synthesis and Stereochemical Assignment of Streptide.Journal of the American Chemical Society · 2019
    Article
  5. Article
  6. 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.

Jeffrey J JacksonDepartment of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA).
Hiroyuki KobayashiDaiichi Sankyo Co., LTD, 1-2-58, Hiromachi, Shinagawa-ku, Tokyo 140-8710 (Japan).
Sophia D SteffensDepartment of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA).
Armen ZakarianDepartment of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106-9510 (USA). zakarian@chem.ucsb.edu.

Funding

Total synthesis of bioactive natural productsR01GM077379 · NIGMS · UNIVERSITY OF CALIFORNIA SANTA BARBARA · PI SERVENT, DENIS, ZAKARIAN, ARMEN · 2008 to 2021
$5.3M
NIGMS NIH HHS R01 GM077379PHS HHS R01-077379
6 · The paper itself

Abstract

The asymmetric synthesis of dragmacidin D (1) was completed in 10 steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6''' position, which is consistent with other members of the dragmacidin family of natural products.

Indexed as

Indole AlkaloidsMolecular ConformationStereoisomerismdragmacidin DIndole Alkaloidsasymmetric synthesisdragmacidinheterocyclesindolestotal synthesis

Identifiers

PMID26130270
PMCPMC4532559

What OpenQuestion holds

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Registered trials

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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.