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Development and Applications of Nove...

Witherspoon, Brittany P.

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Development and Applications of Novel [2+2] and [4+2] Cycloadditions.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Development and Applications of Novel [2+2] and [4+2] Cycloadditions./
Author:	Witherspoon, Brittany P.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	436 p.
Notes:	Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.
Contained By:	Dissertation Abstracts International79-08B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10747617
ISBN:	9780355779653

Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
Witherspoon, Brittany P.

Development and Applications of Novel [2+2] and [4+2] Cycloadditions. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 436 p.

Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.

Thesis (Ph.D.)--Indiana University, 2018.

The enantioselective synthesis of cyclobutane derivatives has been a longstanding interest in organic chemistry. This is due to its synthetic versatility as the cyclobutane framework is susceptible to a variety of transformations towards more complex structures. Additionally, a significant amount of biologically relevant molecules contain the cyclobutane framework. Many of these molecules and their derivatives have emerged as promising candidates in drug discovery because their rigid structures have shown to be a factor in potency. Hence, chiral cyclobutanes and their derivatives have been inspiring targets to pursue in method development.

ISBN: 9780355779653Subjects--Topical Terms:

523952
Organic chemistry.

Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
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245 1 0 $a Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
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300 $a 436 p.
500 $a Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.
500 $a Adviser: Michael K. Brown.
502 $a Thesis (Ph.D.)--Indiana University, 2018.
520 $a The enantioselective synthesis of cyclobutane derivatives has been a longstanding interest in organic chemistry. This is due to its synthetic versatility as the cyclobutane framework is susceptible to a variety of transformations towards more complex structures. Additionally, a significant amount of biologically relevant molecules contain the cyclobutane framework. Many of these molecules and their derivatives have emerged as promising candidates in drug discovery because their rigid structures have shown to be a factor in potency. Hence, chiral cyclobutanes and their derivatives have been inspiring targets to pursue in method development.
520 $a In that regard, the first intramolecular chirality transfer [2+2] cycloaddition of allenic ketones and alkenes has been developed to access chiral cyclobutanes and their derivatives. This method depends upon the enantioselective synthesis of allenic ketones and efficient transfer of chirality from starting material to product. With access to a variety of products from this method, it has been applied to the enantioselective synthesis of benzocyclobutenes, which is difficult to achieve by alternative means, and it has been applied to the enantioselective total synthesis of Cajanusine, which is a complex molecule that exhibits inhibitory action against the development of hepatocellular carcinoma cells.
520 $a A novel [4+2] cycloaddition of alkenylboranes and alkenes has also been developed. This is a significant method because the enantioenriched products accessed are synthetically versatile intermediates that could be obtained in high degrees of enantioselectivity, and because the process provides an interesting mechanistic perspective of alkenylborane-alkene [4+2] cycloadditions using an oxazaborolidine backbone.
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