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Recent advances in the synthesis of 2-pyrones.

Lee JS - Mar Drugs (2015)

Bottom Line: The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products.Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review.

View Article: PubMed Central - PubMed

Affiliation: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology (KIOST), Ansan 426-744, Korea. jslee@kiost.ac.kr.

ABSTRACT
The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products. Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review.

No MeSH data available.


Proposed mechanism.
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marinedrugs-13-01581-f021: Proposed mechanism.

Mentions: The experimentally proven mechanism describes that the reaction is initiated by the magnesium chloride-mediated conversion of glycidic ester (129) to keto ester (A) (Figure 21). Subsequently, elimination of acetone via keto-enol tautomerism results in formation of intermediate D. At this stage, the reaction proceeds in two different plausible pathways. For example, nucleophilic addition of hydroxyl group to ester carbonyl carbon (pathway A) would provide 4-chloro-3-hydroxy-2-pyrone (130) after elimination of MeOH. In contrast, nucleophilic attack at keto carbonyl position (pathway B) would furnish 3-chloro-2-hydroxy-2,5-dihydrofuran-2-carboxylate (F).


Recent advances in the synthesis of 2-pyrones.

Lee JS - Mar Drugs (2015)

Proposed mechanism.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4378001&req=5

marinedrugs-13-01581-f021: Proposed mechanism.
Mentions: The experimentally proven mechanism describes that the reaction is initiated by the magnesium chloride-mediated conversion of glycidic ester (129) to keto ester (A) (Figure 21). Subsequently, elimination of acetone via keto-enol tautomerism results in formation of intermediate D. At this stage, the reaction proceeds in two different plausible pathways. For example, nucleophilic addition of hydroxyl group to ester carbonyl carbon (pathway A) would provide 4-chloro-3-hydroxy-2-pyrone (130) after elimination of MeOH. In contrast, nucleophilic attack at keto carbonyl position (pathway B) would furnish 3-chloro-2-hydroxy-2,5-dihydrofuran-2-carboxylate (F).

Bottom Line: The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products.Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review.

View Article: PubMed Central - PubMed

Affiliation: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology (KIOST), Ansan 426-744, Korea. jslee@kiost.ac.kr.

ABSTRACT
The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products. Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review.

No MeSH data available.