Total synthesis of (±)-nicolaioidesin B via a highly regio- and diastereoselective Diels–Alder reaction

[Display omitted] The total synthesis of (±)-nicolaioidesin B, a natural product that shows preferential cytotoxicity against pancreatic cancer cells under nutrient starvation conditions, is achieved. The key step is a thermally-induced, highly regio- and diastereoselective Diels–Alder reaction betw...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 50; pp. 6864 - 6867
Main Authors Pigott, Adam J., Lepage, Romain J., White, Jonathan M., Coster, Mark J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.12.2014
Elsevier
Subjects
Cancer
Chemistry
Chemistry, Organic
Diels-Alder reactions
Diels–Alder reaction
Natural product
Natural products
Nicolaioidesin B
Nutrients
Panduratin A
Physical Sciences
Science & Technology
Synthesis (chemistry)
Tetrahedrons
CIQQYRZTKOGULG-PQNGQFLHSA-N
Nicolaioidesin B
Panduratin A
QPASIUICYJHVJC-ICBNADEASA-N
OJSFFJVPKJOBSD-VAMGGRTRSA-N
Natural product
Diels–Alder reaction
Cancer
SECONDARY METABOLITES
APOPTOSIS
TOLERANCE
KAEMPFERIA-PANDURATA
INDUCTION
ANGELMARIN
NUTRIENT DEPRIVATION
PROSTATE-CANCER CELLS
Diels-Alder reaction
CYCLOHEXENYL CHALCONE DERIVATIVES
CONSTITUENTS
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Summary:[Display omitted] The total synthesis of (±)-nicolaioidesin B, a natural product that shows preferential cytotoxicity against pancreatic cancer cells under nutrient starvation conditions, is achieved. The key step is a thermally-induced, highly regio- and diastereoselective Diels–Alder reaction between (E)-N-methoxy-N-methylcinnamide and ocimene under solvent-free conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.10.097