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Molecules 2013, 18(10), 12290-12312; doi:10.3390/molecules181012290

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

1
Department of Medicinal Chemistry, Nerviano Medical Sciences srl, Business Unit Oncology, Viale Pasteur 10, 20014 Nerviano, MI, Italy
2
Department of Chemical Core Technologies, Nerviano Medical Sciences srl, Business Unit Oncology, Viale Pasteur 10, 20014 Nerviano, MI, Italy
*
Author to whom correspondence should be addressed.
Received: 24 July 2013 / Revised: 18 September 2013 / Accepted: 23 September 2013 / Published: 8 October 2013
(This article belongs to the Special Issue Named Organic Reactions based on Italian Chemists)

Abstract

Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter- and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.
Keywords: 2-furylcarbinols; pentadienyl cation; prostaglandins; spirocycles; domino reaction 2-furylcarbinols; pentadienyl cation; prostaglandins; spirocycles; domino reaction
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Piutti, C.; Quartieri, F. The Piancatelli Rearrangement: New Applications for an Intriguing Reaction. Molecules 2013, 18, 12290-12312.

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