Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones

Boonsri, Sompong, Gunawan, Christian, Krenske, Elizabeth H. and Rizzacasa, Mark A. (2012) Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones. Organic and Biomolecular Chemistry, 10 30: 6010-6021. doi:10.1039/c2ob25115a


Author Boonsri, Sompong
Gunawan, Christian
Krenske, Elizabeth H.
Rizzacasa, Mark A.
Title Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2012-08-14
Year available 2012
Sub-type Article (original research)
DOI 10.1039/c2ob25115a
Open Access Status Not Open Access
Volume 10
Issue 30
Start page 6010
End page 6021
Total pages 12
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Formatted abstract
The methyl ether derivatives 2, 4 and 6 of the mulberry Diels–Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels–Alder reactivity. Density functional theory calculations show that the OH group lowers the barrier for the Diels–Alder reaction by 2–3 kcal mol−1 compared with OMe. The acceleration by the OH group is traced to two transition-state effects: a stronger diene–chalcone interaction and better planarity of the aryl–diene unit.
Keyword Morus-Alba
Root bark
Macrophomate synthase
Density functionals
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID DP110100112
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
School of Chemistry and Molecular Biosciences
 
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