First total synthesis of prunustatin A

[Display omitted] In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactoniz...

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Published inTetrahedron letters Vol. 55; no. 6; pp. 1175 - 1177
Main Authors Yamakoshi, Shuhei, Kawanishi, Eiji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.02.2014
Elsevier
Subjects
15-Membered ring
Anhydrides
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
GRP78
Inhibitors
Macrocyclization
organic compounds
Physical Sciences
Proteins
Prunustatin A
Reformatsky reaction
Science & Technology
Synthesis (chemistry)
Tetrahedrons
GRP78
Prunustatin A
Reformatsky reaction
Macrocyclization
15-Membered ring
CHAPERONE DOWN-REGULATOR
STREPTOMYCES-VIOLACEONIGER
LACTONIZATION
MIXED ANHYDRIDE
CATALYSTS
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Summary:[Display omitted] In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactonization using 2-methyl-6-nitrobenzoic anhydride (MNBA) and 4-dimethylaminopyridine (DMAP).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.12.106