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Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B

Part of the Springer Theses Book Series

DOI: 10.1007/978-3-642-27195-3

ISBN: 978-3-642-27194-6

Publisher: Springer Berlin Heidelberg - Springer Journals

Jan 15, 2012

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Chapter 1Introduction

Sun, Xiao-Yu

Pages: 1 –19

[Organic peroxides are compounds containing an O–O bond. The O–O group is called the peroxide group. The peroxide bond is one of the weakest bonds in organic molecules, with BDE of approximately 34 kcal/mol (C–C: 81 kcal/mol, C–H: 98 kcal/mol, C–O: 79 kcal/mol, C–N: 66 kcal/mol). The O–O bond is...
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Chapter 2Results and Discussion

Sun, Xiao-Yu

Pages: 21 –76

[Plakortide E (85) and plakortone B (87) were first isolated from the Jamaican marine sponge Plakortis halichondrioides along with plakortones A, C, D in 1996 by Patil and coworkers. In 1999, plakortone B (87) was also isolated from the Caribbean sponge Plakortis simplex along with plakortones...
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Chapter 3Conclusion

Sun, Xiao-Yu

Pages: 77 –78

[The key steps included the synthesis of enantiomerically pure dioxolane cores through lipase resolution of a racemic precursor, the introduction of an alkynyl sidechain on a 1,2-dioxolane via a Corey-Fuchs homologation, and the introduction of the sidechain of the natural product through...
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Chapter 4Experimental Section

Sun, Xiao-Yu

Pages: 79 –126

[All non-aqueous reactions were carried out using oven-dried glassware under a positive pressure of dry nitrogen unless otherwise noted. All reagents and solvents were reagent grade. Further purifications and drying by standard methods were used when necessary. Except as indicated otherwise,...

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