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Biomimetic synthesis of a library of carpanone-like molecules.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Biomimetic synthesis of a library of carpanone-like molecules.
作者:	Chan, Lawrence Kwan Yiu.
面頁冊數:	224 p.
附註:	Adviser: Matthew D. Shair.
附註:	Source: Dissertation Abstracts International, Volume: 64-01, Section: B, page: 0208.
Contained By:	Dissertation Abstracts International64-01B.
標題:	Chemistry, Organic.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3076875
ISBN:	0493973370

Biomimetic synthesis of a library of carpanone-like molecules.
Chan, Lawrence Kwan Yiu.

Biomimetic synthesis of a library of carpanone-like molecules. [electronic resource] - 224 p.

Adviser: Matthew D. Shair.

Thesis (Ph.D.)--Harvard University, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0493973370Subjects--Topical Terms:

193634
Chemistry, Organic.

Biomimetic synthesis of a library of carpanone-like molecules.
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502 $a Thesis (Ph.D.)--Harvard University, 2003.
520 $a *Please refer to dissertation for diagrams.
520 $a The synthesis of a 10,000-member library of molecules bearing the tetracyclic carpanone core is described in this thesis. The synthesis of the carpanone core was inspired by the proposed biosynthesis of the natural product. A PhI(OAc)2 mediated oxidative phenolic coupling reaction was developed to construct a carpanone-like structure. In addition to coupling two identical phenols, this reaction also allows the coupling of two different phenols. A single product was obtained in cases involving two different phenols by manipulating the electronic properties of the coupling partners.*
520 $a Various diversity-generating reactions were used during library thesis. A tandem oxime formation amine 1,4-addition reaction was developed to incorporate an oxime and a secondary amine into the carpanone core. The secondary amines were then converted to a variety of amides, carbamates, ureas and sulfonamides. In a different route, the core was subjected to a thio 1,4-addition reaction followed by oxime formation to incorporate a different set of building blocks. Furthermore a tandem oxime formation azide 1,4-addition was performed on the core. The azide introduced was then converted to triazoles via a cycloaddition reaction with alkynes. Finally, the phenols generated after deallylation of the core were subjected to Mitsunobu reaction, biaryl coupling and carbamate formation to give about 10,000 structurally complex molecules containing a diverse collection of functional groups.
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