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Molecules 2014, 19(4), 5231-5242; doi:10.3390/molecules19045231
Article

The Intramolecular Diels-Alder Reaction of Diarylheptanoids — Quantum Chemical Calculation of Structural Features Favoring the Formation of Phenylphenalenones

1
 and 2,*
Received: 21 January 2014; in revised form: 15 April 2014 / Accepted: 17 April 2014 / Published: 23 April 2014
(This article belongs to the Section Metabolites)
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Abstract: Diarylheptanoids have been reported as biosynthetic precursors of phenylphenalenones in plants. Quantum chemical calculations of molecular geometry and orbitals were used to elaborate which structural features are required to determine if diarylheptanoids can undergo an intramolecular Diel-Alder reaction to form phenylphenalenones. The computational data showed that an ortho-quinone- or a hydoxyketone-bearing ring A, containing the dienophile moiety, and a heptadiene chain with conjugated cisoid double bonds at C-4/C-6 and a saturated segment consisting of two sp3-carbon atoms, are required. Only four diarylheptanoids out of eighteen studied compounds proved to be suitable candidates. Among them are two 3,5-dideoxy compounds and two other compounds oxygenated only at C-3, suggesting that lachnanthocarpone, a representative of the 6-oxygenated phenylphenalenones, and anigorufone, a representative of the 6-deoxy phenylphenalenones, are not connected via a precursor-product relationship (“late reduction at C-6”) but formed through partially separate pathways.
Keywords: diarylheptanoids; (4+2)-cycloaddition; Diels-Alder reaction; phenylphenalenones; quantum chemistry; 6-31G*; molecular orbitals diarylheptanoids; (4+2)-cycloaddition; Diels-Alder reaction; phenylphenalenones; quantum chemistry; 6-31G*; molecular orbitals
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Monakhova, Y.; Schneider, B. The Intramolecular Diels-Alder Reaction of Diarylheptanoids — Quantum Chemical Calculation of Structural Features Favoring the Formation of Phenylphenalenones. Molecules 2014, 19, 5231-5242.

AMA Style

Monakhova Y, Schneider B. The Intramolecular Diels-Alder Reaction of Diarylheptanoids — Quantum Chemical Calculation of Structural Features Favoring the Formation of Phenylphenalenones. Molecules. 2014; 19(4):5231-5242.

Chicago/Turabian Style

Monakhova, Yulia; Schneider, Bernd. 2014. "The Intramolecular Diels-Alder Reaction of Diarylheptanoids — Quantum Chemical Calculation of Structural Features Favoring the Formation of Phenylphenalenones." Molecules 19, no. 4: 5231-5242.


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