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Synthesis of inverto-yuehchukene and substituted 1,2,3,4-tetrahydrocyclopent[b]indole張文驥, Cheung, Man-ki. January 1995 (has links)
published_or_final_version / Chemistry / Doctoral / Doctor of Philosophy
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Total synthesis of indole alkaloids: pt. 1. Asymmetric synthesis of (-)-ibogamine. pt. 2. An approach toward the synthesis of koumineChoi, Younggi 04 February 2003 (has links)
PART I. The preparation of (-)-ibogamine (1) in fourteen steps from
benzoquinone and in 10% overall yield is a powerful illustration of the value of
the asymmetric Diels-Alder reaction as a starting point in a multistep synthesis.
All four cycloadducts, 70, 77, 84 and 96, obtained with the (S)-BINOL-TiCl���
complex were found to have the same absolute configuration. Furthermore, they
are in the same enantiomeric series that Mikami observed with 1,4-naphthoquinone using the same catalyst, lending confidence to future stereochemical predictions that may be made with this system.
PART II. Three different routes for the synthesis of the
hexahydroisoquinoline 98 met obstacles which defeated our approach to
koumine. The Diels-Alder reaction of cyclic 1-azadienes 102 and 108 was
abandoned due to the lack of reactivity of the dienes. An anionic oxy-Cope
rearrangement of the azabicyclo[2.2.2]octane system caused mainly
decomposition of the starting materials. Finally, an intramolecular [2+2]
photocycloaddition generated "crossed", "straight" and hydroisoquinoline
products in varying ratios, depending on the substituent pattern of the substrate,
but this approach was not synthetically useful. The results from this last study
may be valuable for predicting the regiochemical outcome of certain
intramolecular photocycloadditions. / Graduation date: 2003
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Synthetic study of seco-yuehchukene and inverto-yuehchukene李輝途, Lee, Victor. January 1987 (has links)
published_or_final_version / Chemistry / Master / Master of Philosophy
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A general synthetic route to Yuehchukene analogues via 7alpha-methoxycarbonyl-9-methyl-6-oxo-5,6,6abeta,7betaB,8,10aB-hexahydroindeno [2,1-b] indole, and related studies on 1-methoxyindole黃子達, Wong, Tze-tat, Edward. January 1992 (has links)
published_or_final_version / Chemistry / Doctoral / Doctor of Philosophy
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Synthetical experiments related to the indole alkaloids / by David Roland Liljegren.Liljegren, David Roland January 1962 (has links)
Typewritten / 153 leaves / Title page, contents and abstract only. The complete thesis in print form is available from the University Library. / Thesis (Ph.D.)--University of Adelaide, Dept. of Organic Chemistry, 1962
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Studies on diazoketone rearrangements and application toward the synthesis of welwistatinLam, Shuk-mei, 林淑媚 January 2013 (has links)
published_or_final_version / Chemistry / Doctoral / Doctor of Philosophy
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Study of Diels-Alder reactions in the syntheses of Yuehchukene analogues and optically active Yuehchukene曹國安, Cao, Guo-an. January 1993 (has links)
published_or_final_version / Chemistry / Doctoral / Doctor of Philosophy
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The synthesis of 3,5-disubstituted indolizidinesCheesman, Penelope, Sue January 1996 (has links)
A dissertation submitted to the Faculty of Science, University of the
Witwatersrand, Johannesburg, in fulfilment of the requirements for the
degree of Master of Science. January 1996. / Aspects of the literature of the ant venom alkaloid monomorine I and its stereoisomers
were reviewed.
Racemic 5-butyl-2-pyrrolidinone was synthesised in two steps from methyl acrylate and
1-nitropentane, A thionation step yielded 5-butylpyrrolidine-2-thione. The Michael
addition reaction between 5-butylpyrrolidine-2-thione and ethyl crotonate proceeded with
difficulty to form a separable mixture of diastereomers of 5-butyl-l-(2-ethoxycarbonyl-l-methylethyl)
pyrrolidine-2-thione. [Abbreviated Abstract. Open document to view full version] / AC2017
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Novel syntheses of 5- and 7- azaindole derivativesLeboho, Tlabo Caiphus 05 March 2014 (has links)
This thesis describes the application of the Sonogashira coupling reaction to access a variety of
5-and 7-azaindoles derivatives. The background chapter paints a picture about the importance of
indole-containing compounds and azaindole-containing compounds. In this first chapter,
discovery, synthesis, properties and reactivity of indole and azaindoles were explained.
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New methods for the diastereoselective construction of vicinal quaternary stereocenters and their application to the total synthesis of the bioactive (±)-dehalo-perophoramidineWilkie, Ross Philip January 2015 (has links)
This thesis describes a novel total synthesis of (±)-dehalo-perophoramidine (a dehalogenated analogue of the natural product perophoramidine). The key synthetic transformation involves the construction of vicinal quaternary stereocenters which were installed diastereoselectively. A Claisen rearrangement was used to install the first quaternary stereocenter then a Corey-Chaykovsky-type reaction and a Hosomi-Sakurai-type reaction were used to install the second quaternary stereocenter. Investigations directed towards the total synthesis of the communesin family of natural products are also described. In Chapter 1, the natural products perophoramidine and the communesins are introduced and their related biosynthesis is discussed. The isolation, architectural motifs and biological properties of the natural products are described and discussed. Previously reported approaches to perophoramidine and the communesins are reviewed focussing on how the vicinal quaternary stereocenters are formed in each case. Chapter 1 concludes with the retrosynthetic plan used to form dehalo-perophoramidine. In Chapter 2, previous research from the Westwood group is reviewed focusing on an asymmetric Claisen rearrangement which could potentially be used to install a quaternary stereocenter asymmetrically. A previously reported novel Cope rearrangement, potentially useful for a communesin synthesis, is optimised using microwave, neat and high-temperature flow conditions and leads to the synthesis of an intermediate containing two allyl substituents. In Chapter 3, attempts to functionalise selectively the two allyl substituents are described which was eventually achieved by a regioselective iodoetherification reaction. This leads to the synthesis of two relatively advanced intermediates for a communesin synthesis. Although the total synthesis of the communesins was not achieved, a proposed route from the advanced intermediates to the natural products is described. In Chapter 4, a novel method to construct vicinal quaternary stereocenters is disclosed using a Corey- Chaykovsky-type reaction and a Hosomi-Sakurai-type reaction. A regioselective iodolactonisation, analogous to that presented in Chapter 3, is used to functionalise selectively two allyl substituents that culminates in the preparation of a pentacyclic lactam. In Chapter 5, the total synthesis of (±)-dehalo-perophoramidine is completed and its structure is confirmed by a NMR doping experiment with an authentic sample. The biological activity of dehalo- perophoramidine is investigated and compared to that of perophoramidine. Chapter 5 culminates in an attempted synthesis of the natural product perophoramidine using the route that was used to make dehalo-perophoramidine.
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