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Stereoselective Synthesis of Butenol...

Li, Yi.

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Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials./
Author:	Li, Yi.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2017,
Description:	264 p.
Notes:	Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.
Contained By:	Dissertation Abstracts International79-02B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10263124
ISBN:	9780355260366

Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials.
Li, Yi.

Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials. - Ann Arbor : ProQuest Dissertations & Theses, 2017 - 264 p.

Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.

Thesis (Ph.D.)--University of Delaware, 2017.

Allyl cyclopropene carboxylates undergo ring expansion reaction to give alloxyfuran intermediates, which can further rearrange to Deltabeta, gamma butenolides via Claisen rearrangement or Deltaalpha, beta butenolides via a further Cope rearrangement. These reactions display catalyst dependent regioselectivity and is stereospecific. The transition state was proposed and supported by absolute stereochemistry assignment. This method was applied to the total synthesis of dehydro-sessilifoliamide C. It features an one step installation of all the connectivities and a short and efficient synthesis of the cyclopropene carboxylate. Attempts to prepare sessilifoliamide B by hydrogenation were unsuccessful.

ISBN: 9780355260366Subjects--Topical Terms:

523952
Organic chemistry.

Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials.
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100 1 $a Li, Yi. $3 911053
245 1 0 $a Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2017
300 $a 264 p.
500 $a Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.
500 $a Adviser: Joseph Fox.
502 $a Thesis (Ph.D.)--University of Delaware, 2017.
520 $a Allyl cyclopropene carboxylates undergo ring expansion reaction to give alloxyfuran intermediates, which can further rearrange to Deltabeta, gamma butenolides via Claisen rearrangement or Deltaalpha, beta butenolides via a further Cope rearrangement. These reactions display catalyst dependent regioselectivity and is stereospecific. The transition state was proposed and supported by absolute stereochemistry assignment. This method was applied to the total synthesis of dehydro-sessilifoliamide C. It features an one step installation of all the connectivities and a short and efficient synthesis of the cyclopropene carboxylate. Attempts to prepare sessilifoliamide B by hydrogenation were unsuccessful.
520 $a The third chapter describes a collaborative research on the development of biomaterial for cell culture purpose using tetrazine ligation. The chapter describes the development of chemical tools for the hydrogel preparation. The mechanical properties of hydrogels were controlled by introducing capping groups alongside crosslinker molecules in interfacial crosslinking events. Enzyme degradable crosslinkers and cell adhesive signals are prepared and introduced to the gels. It was shown by my collaborator that all the newly developed chemical tools can be incorporated in to the HA-Tz based hydrogels and NIH 3T3 cells can be cultured in the system with good viability and morphology.
590 $a School code: 0060.
650 4 $a Organic chemistry. $3 523952
650 4 $a Materials science. $3 543314
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710 2 $a University of Delaware. $b Chemistry and Biochemistry. $3 3174095
773 0 $t Dissertation Abstracts International $g 79-02B(E).
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791 $a Ph.D.
792 $a 2017
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10263124