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

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

1
Department of Chemistry, Saratov State University, Astrakhanskaya Street 83, Saratov 410012, Russia
2
Max Planck Institute for Chemical Ecology, Hans Knöll-Str. 8, Jena 07745, Germany
*
Author to whom correspondence should be addressed.
Received: 21 January 2014 / Revised: 15 April 2014 / Accepted: 17 April 2014 / Published: 23 April 2014
(This article belongs to the Section Natural Products)
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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
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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.

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