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Studies on the Phenolic Antioxidants from Smilax Glyciphylla and the Synthesis and Formation of Guaiane Sesquiterpenoids

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Studies on the Phenolic Antioxidants from Smilax Glyciphylla and the Synthesis and Formation of Guaiane Sesquiterpenoids Natural Product Discovery: Studies on the Phenolic Antioxidants from Smilax Glyciphylla and the Synthesis and Formation of Guaiane Sesquiterpenoids. A thesis presented in fulfilment of the requirements for the degree of Doctor of Philosophy by Ancheng Huang BE (South China Agricultural University) Graduate (South China University of Technology) School of Agriculture, Food and Wine Faculty of Sciences The University of Adelaide September 2014 Table of Contents Abstract ..................................................................................................................................... v List of Publications ................................................................................................................ vii Declaration............................................................................................................................ viii Acknowledgements ................................................................................................................. ix Abbreviations .......................................................................................................................... xi Chapter 1. Introduction to Natural Products ............................................................................ 1 1.0 The emergence of natural products. ................................................................................. 1 1.1 The discovery process of NP and novel techniques developed for NP research. ............ 3 1.2 Natural product synthesis. ................................................................................................ 6 1.3 The total synthesis of Taxol as an exemplar. ................................................................... 7 1.3.1 Holton Taxol total synthesis. ..................................................................................... 8 1.3.2 Nicolaou Taxol total synthesis. ............................................................................... 10 1.3.3 Danishefsky’s Taxol total synthesis. ....................................................................... 12 1.3.4 Wender Taxol total synthesis-the pinene path. ........................................................ 14 1.3.5 Kuwajima Taxol total synthesis. ............................................................................. 16 1.3.6 Mukaiyama Taxol total synthesis. ........................................................................... 18 1.3.7 Takahashi Taxol total synthesis. .............................................................................. 18 1.4 Semi-synthesis of Taxol and side chain strategies. ........................................................ 20 1.5 Biosynthesis of Taxol. .................................................................................................... 33 1.6 Summary. ....................................................................................................................... 36 1.7 Aims of this thesis. ......................................................................................................... 36 1.8 References for Chapter 1. ............................................................................................... 41 Chapter 2. Examination of the Phenolic Profile and Antioxidant Activity of the Leaves of the Australian Native Plant Smilax glyciphylla ....................................................................... 48 Chapter 3. Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi- Melicodenone C and E and other Guaiane-type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol. ............................................................................................................. 58 Chapter 4. Production of the Pepper Aroma Compound, (-)-Rotundone by Aerial Oxidation of α-Guaiene. ........................................................................................................................... 75 ii Chapter 5. Mechanistic Studies on the Autoxidation of α-Guaiene: The Structural Diversity of the Sesquiterpenoid Downstream Products. ........................................................................ 84 Chapter 6. Rationalizing the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions: Synthesis of Deuterium Labelled Analogues and SIDA/GC-MS Studies. ................................................................... 122 Chapter 7. Conclusions......................................................................................................... 142 List of Figures and Schemes for Chapter 1 Figure 1. Structures of some typical natural product drugs. ..................................................... 2 Figure 2. Generic NP based drug discovery process. ............................................................... 4 Figure 3. Different synthetic strategies in the total synthesis of Taxol. .................................... 8 Figure 4. Putative Taxol biosynthetic pathway. ...................................................................... 35 Figure 5. Plausible D ring formation pathway via epoxy fragmentation. .............................. 36 Figure 6. TLC and HPLC trace of the butanol fraction of the ethanolic extract of the leaves of Smilax glyciphylla. ............................................................................................................... 37 Figure 7. Proposed synthetic route to guaiol isomers, natural melicodenones C and E and their C1 epimers via the diastereoselective epoxidation of guaiol. ......................................... 38 Figure 8. GC trace of products of oxidation of neat α-guaiene with pure O2 at room temperature for 40 days. .......................................................................................................... 40 Scheme 1. The Holton Taxol total synthesis. ............................................................................ 9 Scheme 2. The Nicolaou Taxol total synthesis. ...................................................................... 11 Scheme 3. The Danishefsky Taxol total synthesis. ................................................................. 13 Scheme 4. The Wender Taxol total synthesis. ........................................................................ 15 Scheme 5. The Kuwajima Taxol total synthesis. .................................................................... 17 Scheme 6. The Mukaiyama Taxol total synthesis. .................................................................. 19 Scheme 7. The Takahashi Taxol total synthesis. ..................................................................... 20 Scheme 8. Greene’s side chain synthesis via azide-induced epoxy ring opening in 1986. ..... 21 Scheme 9. Sharpless’s side chain synthesis through asymmetric dihydroxylation in 1994. ... 22 Scheme 10. Jacobsen’s Taxol semisynthesis through asymmetric epoxidation in 1992. ....... 22 Scheme 11. Greene’s side chain synthesis from phenylglycine in 1992. ................................ 23 iii Scheme 12. Greene’s Taxol side chain synthesis from Oppozler’s camphorsultam in 1994. 23 Scheme 13. Commerçon’s side chain synthesis in 1992. ........................................................ 24 Scheme 14. Holton β-lactam synthesis in 1990. ...................................................................... 25 Scheme 15. Ojima Taxol side chain synthesis via β-lactam in 1992. ..................................... 25 Scheme 16. Farina’s taxol side chain synthesis in 1992. ........................................................ 26 Scheme 17. Georg’s taxol side chain synthesis in 1992. ......................................................... 26 Scheme 18. Hanaoka’s Taxol side chain synthesis via aldol condensation in 1992. .............. 27 Scheme 19. Chen’s side chain synthesis in 1993. ................................................................... 27 Scheme 20. Yamamoto’s side chain synthesis in 1993. .......................................................... 28 Scheme 21. Gennari’s side chain thioester oxazolidine synthesis in 1996. ............................ 28 Scheme 22. Kingston’s oxazolidine synthesis in 1999. .......................................................... 29 Scheme 23. Greene and Portier’s Taxol semisynthesis via direct esterification in 1988. ....... 30 Scheme 24. Greene’s improved Taxol semisynthesis via oxazolidine coupling in 1994. ...... 30 Scheme 25. Commerçon’s Taxol semisynthesis via oxazolidine coupling in 1992. ............... 31 Scheme 26. Holton, Ojima and Georg’s Taxol semisynthesis via β-lactam coupling. ........... 32 Scheme 27. Gennari’s Taxol semisynthesis via thioester coupling. ....................................... 32 Scheme 28. NPI’s commercialised Taxol semi-synthesis. ...................................................... 32 iv Abstract The work within this thesis is positioned in the field of natural product (NP) chemistry and covers three main integrated studies along with some additional explorations. These studies not only included the isolation and characterisation of NP but also involved total syntheses of various NP and related derivatives and detailed mechanistic studies into potential routes of formation in nature. Given my naturally emerging zest for natural products, I have begun this thesis with a detailed discussion of the numerous syntheses of Taxol. This exemplar highlights not only why the field of natural products is so important, but also highlights the ever growing significance of
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