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Abstract
Chapter one of this dissertation gives an overview of current methods for the synthesis of epoxy alcohols. It outlines our development and application of a convenient one-pot method for the synthesis of epoxy alcohols and allylic epoxy alcohols in excellent yield, enatioselectivities and diastereoselectivites. Our method for the synthesis of epoxy alcohols offers several advantages over existing methods. These advantages, as well as the limitations of our protocol are outlined in this chapter.
Chapter two encompasses our expansion of our oxidation methods to encompass pyranones. Our development of a one-pot method for the synthesis of pyranones is outlined. Our protocol uses an asymmetric C-C bond forming reaction, followed by oxidation with NBS to get pyranone products in excellent yield and enatioselectivies.
Chapter three gives a detailed account of our development and application of a new organic reaction for the synthesis of 2-substituted, 3-formyl furans and 3-formyl pyrroles. This protocol starts with formation of a 3-furyl alcohol or tosyl amine followed by oxidation using NBS to form the 2-substtuted 3-formyl furan or pyrrole. We have applied this method to the synthesis of chiral furyl 3-formyl furans.
