2005•Angewandte Chemie International EditionRequires access

Biomimetic Total Synthesis of Gambogin and Rate Acceleration of Pericyclic Reactions in Aqueous Media

K. C. Nicolaou, Hao Xu, Markus Wartmann

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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Key concepts: Pericyclic reaction, Claisen rearrangement, Acceleration, Total synthesis, Cascade, Cascade reaction, Chemistry, Sequence (biology)