Inverse electron demand diels-alder based approach to 6H-Dibenzo[b, d]pyran-6-ones and its application in target-oriented synthesis

Nandaluru, Penchal Reddy (2012) Inverse electron demand diels-alder based approach to 6H-Dibenzo[b, d]pyran-6-ones and its application in target-oriented synthesis. Doctoral (PhD) thesis, Memorial University of Newfoundland.

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Abstract

This thesis deals with the exploration and the development of Inverse Electron-Demand Diels-Alder (IEDDA)-based methodologies to access 6H-dibenzo[b,d]pyran-6-ones (DBPs) and their application in target-oriented synthesis. Due to its importance throughout this dissertation, the Diels-Alder reaction is discussed in some detail in Chapter 1. This is followed by a discussion of the evolution of research on the IEDDA reaction in the Bodwell group. A detailed investigation of the methods that were developed to produce DBPs is described in Chapter 2 and Chapter 3. Furthermore, the scope of these methodologies was demonstrated by applying these approaches to the synthesis of natural and non-natural products. In this regard, their use in the synthesis of elaborated chiral pyrenophanes (non-natural products) is presented in Chapter 4, and their application in the synthesis of natural products such as Cannabinol and Defucogilvocarcin V is displayed in Chapter 2 and Chapter 5.

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