Conioidine A (1), isolated in 1993 with unknown relative and absolute configuration, was suggested to be a DNA-binding compound by an indirect technique. Four stereoisomers of conioidine A have been synthesized from D-and L-proline, and the natural product has been identified as possessing (4R,6R) absolute configuration. Binding of the conioidine diastereomers to calf thymus DNA (CT DNA) and human serum albumin (HSA) has been investigated by fluorescence spectroscopy and isothermal titration calorimetry (ITC). All stereoisomers display at least an order of magnitude weaker binding to DNA than the control compound netropsin; however, a strong association with HSA was observed for the (4R,6S) stereoisomer.

CHAPTER 2: METHODOLOGY IN ANTHRONE C-GLYCOSIDE SYNTHESIS 2.1 Introduction………………………………………………………..……………..……8 2.2 Alkylation of anthrones………..……………………………………………………....8 2.3 In-vitro biosynthesis of the C-glycosidic bond in aloin …………………...….………8 2.4 Total synthesis of cassialoin……………………………….…………………..……...9 CHAPTER 3: SYNTHESIS OF ALVARADOINS E & F, UVEOSIDE, AND 10-EPI-UVEOSIDE 3.1 Introduction…………………………………………..………....………………...…11 3.2 Objectives and retrosynthetic analysis ………...…………………………….………12 3.3 Synthesis of fragment 8……………………………………………………...………13 3.4 Synthesis of fragment 9a…………………………………………………….………13 3.5 Model studies for the formation of anthrone-C-glycoside……...…..……….………14 3.6 Formation of carboxylic acid intermediate ………………………………………….17 3.7 Conversion to anomeric acetate………………………………………….…………..18 3.8 Hydrolysis of isobutyrate and acetate esters…………………………………………20 vi 3.9 Completion of the synthesis of alvaradoins E and F…..……………………………..21 3.10 Completion of the synthesis of uveoside and 10-epi-uveoside……………...……...22 CHAPTER 4: CONCLUSION …………………………………….

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