Triple

T19066445
Position Surface form Disambiguated ID Type / Status
Subject Corey–Nicolaou macrolactonization E466669 entity
Predicate relatedTo P37 FINISHED
Object Yamaguchi macrolactonization
Yamaguchi macrolactonization is a widely used organic synthesis method for forming large-ring lactones via intramolecular esterification activated by a mixed anhydride, particularly valuable in complex natural product synthesis.
E1356975 NE FINISHED

How this triple was built (4 steps)

Every LLM step that produced this triple, in pipeline order — named-entity classification, the disambiguation choices (the exact options shown, with the pick highlighted), and the generated description. The batch + timestamp of each is in the Provenance table below.

NER Named-entity recognition gpt-5-mini
Instruction
Given a phrase, classify it is english named entity (e.g., persons, organizations, works of art) in Latin script, or not (e.g., literals, dates, URLs, verbose phrases). For disambiguation, the statement where the phrase occurs as object is also given. Please return a JSON object with `phrase` (string, the phrase being analyzed) and `is_ne` (boolean, indicating whether the phrase is a Named Entity).
Input
Phrase: Yamaguchi macrolactonization | Statement: [Corey–Nicolaou macrolactonization, relatedTo, Yamaguchi macrolactonization]
NED1 Entity disambiguation (via context triple) gpt-5-mini-2025-08-07
Target entity: Yamaguchi macrolactonization
Context triple: [Corey–Nicolaou macrolactonization, relatedTo, Yamaguchi macrolactonization]
  • A. Corey–Nicolaou macrolactonization
    Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
  • B. Eschenmoser sulfide contraction
    Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
  • C. Tsuji–Trost reactions
    Tsuji–Trost reactions are palladium-catalyzed allylic substitution processes widely used in organic synthesis to form carbon–carbon and carbon–heteroatom bonds with high regio- and stereocontrol.
  • D. Stork enamine reaction
    The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
  • E. Corey–Winter olefin synthesis
    Corey–Winter olefin synthesis is an organic reaction that converts 1,2-diols into alkenes via cyclic thiocarbonate intermediates, widely used for stereospecific formation of double bonds.
  • F. None of above. chosen
  • G. Unsure - the case is ambiguous/there is not enough information to decide.
NEDg Description generation gpt-5.1
Instruction
Generate a one-sentence description of the target entity. 
You are given a context triple in the form (subject, predicate, object), where the object is the target entity. 
# Instructions
Use the triple to infer relevant information about the entity. Describe the entity based on what is most defining, well-known. 
Avoid repeating the information from the triple, unless really essential.
# Response Format
Return only the sentence: "Description: [one-sentence description of the target entity]"
Input
Entity: Yamaguchi macrolactonization
Triple: [Corey–Nicolaou macrolactonization, relatedTo, Yamaguchi macrolactonization]
Generated description
Yamaguchi macrolactonization is a widely used organic synthesis method for forming large-ring lactones via intramolecular esterification activated by a mixed anhydride, particularly valuable in complex natural product synthesis.
NED2 Entity disambiguation (via description) gpt-5-mini-2025-08-07
Target entity: Yamaguchi macrolactonization
Target entity description: Yamaguchi macrolactonization is a widely used organic synthesis method for forming large-ring lactones via intramolecular esterification activated by a mixed anhydride, particularly valuable in complex natural product synthesis.
  • A. Corey–Nicolaou macrolactonization
    Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
  • B. Eschenmoser sulfide contraction
    Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
  • C. Tsuji–Trost reactions
    Tsuji–Trost reactions are palladium-catalyzed allylic substitution processes widely used in organic synthesis to form carbon–carbon and carbon–heteroatom bonds with high regio- and stereocontrol.
  • D. Stork enamine reaction
    The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
  • E. Corey–Winter olefin synthesis
    Corey–Winter olefin synthesis is an organic reaction that converts 1,2-diols into alkenes via cyclic thiocarbonate intermediates, widely used for stereospecific formation of double bonds.
  • F. None of above. chosen

Provenance (5 batches)

The batch behind each pipeline step, in order, with when it ran. Timestamps are batch-level — stages were processed in waves, so the object chain (NER → NED1 → NEDg → NED2) reads in order, but predicate / elicitation batches can sit in a different wave.

Step Stage Batch ID Status When
creating Elicitation batch_69d8dd04f4488190b1121cc53ef2bfd6 completed April 10, 2026, 11:20 a.m.
NER Named-entity recognition batch_69e5e198621481908618f65dd01746fc completed April 20, 2026, 8:19 a.m.
NED1 Entity disambiguation (via context triple) batch_6a05d3586fc88190b7e48c4afb767a2a completed May 14, 2026, 1:51 p.m.
NEDg Description generation batch_6a05d430aabc8190bdf30a16700e2476 completed May 14, 2026, 1:54 p.m.
NED2 Entity disambiguation (via description) batch_6a05d4e41f108190a2d7a3a60d1e3b87 completed May 14, 2026, 1:57 p.m.
Created at: April 10, 2026, 12:03 p.m.