Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media

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Abstract

A significant rate acceleration of a Claisen rearrangement and of a Claisen/Diels-Alder reaction cascade sequence was observed in the presence of water. This reaction sequence was used in a total synthesis of gambogin (1) from a tricyclic dialkene 3 via 2.

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Nicolaou, K. C., Xu, H., & Wartmann, M. (2005). Biomimetic total synthesis of gambogin and rate acceleration of pericyclic reactions in aqueous media. Angewandte Chemie - International Edition, 44(5), 756–761. https://doi.org/10.1002/anie.200462211

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