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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:	Language materials, manuscript : 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.
Description:	1 online resource (264 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-02(E), Section: B.
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
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. - 1 online resource (264 pages)

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

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

Includes bibliographical references

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.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2018

Mode of access: World Wide Web

ISBN: 9780355260366Subjects--Topical Terms:

1148722
Organic chemistry.
Index Terms--Genre/Form:

554714
Electronic books.

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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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.
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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.
504 $a Includes bibliographical references
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.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2018
538 $a Mode of access: World Wide Web
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710 2 $a University of Delaware. $b Chemistry and Biochemistry. $3 1187217
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