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Synthetic studies of munchnone react...

Lopchuk, Justin M.

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Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products./
作者:	Lopchuk, Justin M.
面頁冊數:	585 p.
附註:	Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.
Contained By:	Dissertation Abstracts International75-06B(E).
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3613745
ISBN:	9781303773518

Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products.
Lopchuk, Justin M.

Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products. - 585 p.

Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.

Thesis (Ph.D.)--Dartmouth College, 2013.

Chapter 1: Munchnones and Mesoionic Heterocycles: The reactivity, regioselectivity, and synthetic applications of munchnones (1,3- oxazolium-5-olates) is a common theme which runs through Chapters 2-5. The definition, structure, and reactivity of mesoionic heterocycles is discussed. The synthesis and reactivity of sydnones, isomunchnones, and munchnones is presented.

ISBN: 9781303773518Subjects--Topical Terms:

516206
Chemistry, Organic.

Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products.
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245 1 0 $a Synthetic studies of munchnone reactivity and applications and the total synthesis of cyclopenta[b]indole natural products.
300 $a 585 p.
500 $a Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.
500 $a Adviser: Gordon W. Gribble.
502 $a Thesis (Ph.D.)--Dartmouth College, 2013.
520 $a Chapter 1: Munchnones and Mesoionic Heterocycles: The reactivity, regioselectivity, and synthetic applications of munchnones (1,3- oxazolium-5-olates) is a common theme which runs through Chapters 2-5. The definition, structure, and reactivity of mesoionic heterocycles is discussed. The synthesis and reactivity of sydnones, isomunchnones, and munchnones is presented.
520 $a Chapter 2: What Controls the Regiochemistry in 1,3-Dipolar Cycloaddition of Munchnones with beta-Nitrostyrenes? The factors which govern the regioselectivity of the reaction between munchnones and dipolarophiles is a long standing question in organic chemistry and has limited the ability of chemists to predict the outcome of reactions and to design reliable munchnone-based syntheses. In most cases, FMO theory fails to account for the formation of the experimentally observed major product. An extensive synthetic study of the 1,3-dipolar cycloaddition between two regioisomeric munchnones and a series of beta-nitrostyrene derivatives is presented; this is coupled with a DFT study which correctly predicts the experimentally observed major products, and an ADF study, which demonstrates that regioselectivity is governed by steric factors and the reorganization energy of the reactants, which overwhelms the effects of orbital overlap.
520 $a Chapter 3: Synthesis of Heteroaryl-substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Munchnones with Nitrovinyl Heterocycles: Aryl- and heteroaryl-substituted pyrroles are valuable synthetic scaffolds which find broad applicability in medicine and materials science. Both symmetrical and unsymmetrical munchnones are allowed to react with a series of nitrovinyl heterocycles resulting in the preparation of a library of substituted pyrroles. The reaction between unsymmetrical munchnones and 2-(nitrovinyl)pyridine and 2-(nitrovinyl)quinoline afforded the corresponding pyrroles in excellent yield with outstanding regioselectivity.
520 $a Chapter 4: A Novel Synthesis of Isoindoles and Azaisoindoles via the 1,3-Dipolar Cycloaddition of Munchnones with Arynes: Due to their poor stability and challenging isolation, few convenient methods exist for the synthesis of isoindole derivatives. The outcome of the reaction between munchnones and arynes is discussed. The reaction conditions can be tuned to selectively generate either isoindoles and azaisoindoles or the product of aryne addition to isoindoles: 9,10- epiminoanthracene derivatives.
520 $a Chapter 5: Synthesis of Atorvastatin via a Late-Stage, Regioselective Munchnone Cyclization: Atorvastatin is one of the best selling drugs on the market today. Previous studies into the preparation of its functionalized pyrrole core via the 1,3-dipolar cycloaddition of munchnones and dipolarophiles resulted in low yields and poor regioselectivity during the event. The development of a new synthesis of atorvastatin via a late-stage, functionality-dense, regioselective munchnone cyclization will be presented. Protected atorvastatin was generated as a single isomer in 91% yield; only a deprotection step is required to furnish atorvastatin.
520 $a Chapter 6: Manganese(III)-mediated oxidative radical addition of malonates to 2- cyanoindole: Cyanoindoles are underutilized scaffolds which, due to their electron-deficient nature, offer contrasting modes of reactivity compared to indole. While some work has been directed toward the functionalization of the related nitroindoles, few methods have been developed which allow for the elaboration of cyanoindoles. The manganese(III) acetatepromoted radical addition of malonates to cyanoindoles is discussed. By taking advantage of the radical stabilizing captodative effect, cyanoindoles are directly functionalized at C-- 3 in moderate to good yields. Several structures, including that of an overoxidation product, are confirmed by X-ray crystallography.
520 $a Chapter 7: Formal Synthesis of Cyclopenta[b]indole Natural Products: Scytonemin and Nostodione A: Scytonemin is a dimeric indole alkaloid isolated from cyanobacteria, which has been shown to have significant UV-radiation absorbing properties. The only previous total synthesis of scytonemin generated the key dihydrocyclopenta[b]indol-2(1H)-one monomer in seven steps (19% overall yield). A new formal synthesis of scytonemin is presented; the key monomer is prepared in only three steps (61% overall yield) by a Aldol-Fischer Indolization-Oxidation sequence.
520 $a Chapter 8: A Short, Protecting Group-Free Total Synthesis of Bruceollines D, E, and J: The bruceollines are naturally-occurring cyclopenta[ b]indoles isolated from Brucea sp. plants which are used natively to treat numerous parasitic diseases including malaria. A short, protecting group-free total synthesis of bruceollines D, E, and J is presented. Bruceolline D is prepared in two steps from commercially available 2,2- dimethylcyclopentanone; selective oxidation of bruceolline D affords bruceolline E; chemoselective reduction of bruceolline E furnishes rac-bruceolline J. Both enantiomers of bruceolline J were prepared for the first time via a chemo- and enantioselective reduction with beta-chlorodiisopinocampheylborane (98% ee). Each bruceolline structure was confirmed by X-ray crystallography.
590 $a School code: 0059.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, General. $3 1021807
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710 2 $a Dartmouth College. $b Chemistry. $3 1029796
773 0 $t Dissertation Abstracts International $g 75-06B(E).
790 $a 0059
791 $a Ph.D.
792 $a 2013
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3613745