Formation of 2-halomethylene-4-cyclopentene-1,3-diones and/or 2-halo-1,4-benzoquinones via ring-expansion of 4-ethynyl-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones. Total synthesis of methyl linderone

An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone. [Display omitted]

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 44; pp. 9284 - 9293
Main Authors Yin, Hong, Dantale, Shubhada W., Akhmedov, Novruz G., Söderberg, Björn C.G.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.11.2013
Elsevier
Subjects
2-Alkylidene-1,3-cyclopentendiones
Alkynylcyclobutenones
Chemistry
Chemistry, Organic
Formations
Methyl linderone
N-Halosuccinimide
Physical Sciences
Rearrangement
Science & Technology
Synthesis
Tetrahedrons
HAAORFVRIYZWEV-YRNVUSSQSA-N
Alkynylcyclobutenones
KRESCVOPSBEKCL-UHFFFAOYSA-N
2-Alkylidene-1,3-cyclopentendiones
Methyl linderone
PWDFSVZEJSQFGK-UHFFFAOYSA-N
N-Halosuccinimide
Rearrangement
ACID
ERYTHROCARPA
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Summary:An in-depth study of the reactions of 4-(ethynyl)-4-hydroxy-2,3-substituted-2-cyclobuten-1-ones with N-bromo- or N-iodosuccinimide, affording in most cases 2-halomethylene-4-cyclopentene-1,3-dione, is described. This reaction was used in a short total synthesis of methyl linderone. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.08.050