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Literature DB >> 20704450

Short synthesis of the seed germination inhibitor 3,4,5-trimethyl-2(5H)-furanone.

Riccardo Surmont¹, Guido Verniest, Norbert De Kimpe.

Abstract

3,4,5-Trimethyl-2(5H)-furanone, a new seed germination inhibitor with very promising agrochemical applications, was efficiently synthesized from 2,3-dimethylmaleic anhydride via nucleophilic addition of methyllithium followed by reduction using sodium borohydride. This two-step synthesis is straightforward and high-yielding and permits the large-scale preparation of the seed germination inhibitor.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20704450 DOI： 10.1021/jo1010476

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

7 in total

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Journal: Plant Physiol Date: 2012-06-21 Impact factor: 8.340

2. F-box protein MAX2 has dual roles in karrikin and strigolactone signaling in Arabidopsis thaliana.

Authors: David C Nelson; Adrian Scaffidi; Elizabeth A Dun; Mark T Waters; Gavin R Flematti; Kingsley W Dixon; Christine A Beveridge; Emilio L Ghisalberti; Steven M Smith
Journal: Proc Natl Acad Sci U S A Date: 2011-05-09 Impact factor: 11.205

3. A Raf-like kinase is required for smoke-induced seed dormancy in Arabidopsis thaliana.

Authors: Inhye Lee; Eunsun Kim; Soobin Choi; Dayoung Kim; Wangyu Hong; Jungki Choi; Hyunmo Choi; Jimin Kim; Ganesh A Sable; Kesavan Markkandan; Dongyeol Lim; Soon Ki Park; Soo Young Kim; Sumin Lee; Moon-Soo Soh
Journal: Proc Natl Acad Sci U S A Date: 2021-04-06 Impact factor: 11.205

4. An efficient and facile synthesis of 3-amino-5-chromenyl-butenolides from 3-formyl chromone, dialkyl acetylenedicarboxylate, and primary amines.

Authors: Saeed Balalaie; Morteza Ashouriha; Frank Rominger; Hamid Reza Bijanzadeh
Journal: Mol Divers Date: 2013-01-23 Impact factor: 2.943

Short synthesis of the seed germination inhibitor 3,4,5-trimethyl-2(5H)-furanone.

1. Structure-activity relationship studies of strigolactone-related molecules for branching inhibition in garden pea: molecule design for shoot branching.

2. F-box protein MAX2 has dual roles in karrikin and strigolactone signaling in Arabidopsis thaliana.

3. A Raf-like kinase is required for smoke-induced seed dormancy in Arabidopsis thaliana.

4. An efficient and facile synthesis of 3-amino-5-chromenyl-butenolides from 3-formyl chromone, dialkyl acetylenedicarboxylate, and primary amines.

5. Strigolactone Analogues with a D-Ring Modified at C-2.

6. Hybrid-type strigolactone analogues derived from auxins.

7. Identification of Volatiles of the Dinoflagellate Prorocentrum cordatum.