Evidence map›Paper›PMID 25756504›Full record

ArticleJournal of the American Chemical Society2015

The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.

Artem Shvartsbart, Amos B Smith

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing 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

14 citing papers in PubMed.

  1. Total Synthesis of Calyciphylline F.Angewandte Chemie (International ed. in English) · 2025
    Article
  2. Article
  3. Article
  4. The Latest Progress in the Chemistry ofMolecules (Basel, Switzerland) · 2024
    Review
  5. Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Review
  14. 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.

Artem ShvartsbartDepartment of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
Amos B SmithDepartment of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.

Funding

SYNTHESIS OF PHYLLANTHOSIDE RELATED ANTITUMOR AGENTSR01CA019033 · NCI · UNIVERSITY OF PENNSYLVANIA · PI SMITH, AMOS B · 1985 to 2024
$5.9M
NCI NIH HHS CA-19033NCI NIH HHS R01 CA019033
6 · The paper itself

Abstract

Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester.

Indexed as

AlkaloidsCarboxylic AcidsChemistry Techniques, SyntheticCyclopentanesEpoxy CompoundsEstersHydrogenationPolycyclic CompoundsStereoisomerismAlkaloidscalyciphylline NCarboxylic AcidsCyclopentanescyclopentenoneEpoxy CompoundsEstersPolycyclic Compounds

Identifiers

PMID25756504
PMCPMC4394112

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.