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Intramolecular Michael reactions of ...

Korboukh, Ilia.

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Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline./
Author:	Korboukh, Ilia.
Description:	201 p.
Notes:	Source: Dissertation Abstracts International, Volume: 71-09, Section: B, page: 5470.
Contained By:	Dissertation Abstracts International71-09B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3420168
ISBN:	9781124167039

Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline.
Korboukh, Ilia.

Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline. - 201 p.

Source: Dissertation Abstracts International, Volume: 71-09, Section: B, page: 5470.

Thesis (Ph.D.)--The Pennsylvania State University, 2010.

We have developed novel methodology that produced the first examples of intramolecular 1,4-conjugate additions of carbon and hetero nucleophiles to vinylnitroso compounds. Combining several new methods developed in these labs, we have been able to access the requisite precursors and optimize the reaction conditions for these transformations. Namely, we have shown that a vinylnitroso species generated from the corresponding alpha-chlorosilyl-oximes using fluoride ion, interacts with a tethered nucleophile in a 1,4-manner producing a variety of carbocyclic and heterocyclic products. Recognizing that this methodology allows us facile entry into the stemofoline alkaloid skeleton, we have attempted to apply it to an asymmetric total synthesis of this metabolite. In the course of these studies new methodology for oxidation of alpha-hydroxy-beta-ketoesters to alpha-diazo-beta-ketoesters emerged, thus allowing us to generate some of the intermediates required to advance the synthesis.

ISBN: 9781124167039Subjects--Topical Terms:

516206
Chemistry, Organic.

Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline.
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020 $a 9781124167039
035 $a (UMI)AAI3420168
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100 1 $a Korboukh, Ilia. $3 1682400
245 1 0 $a Intramolecular Michael reactions of vinylnitroso compounds and studies directed towards an asymmetric total synthesis of the Stemona alkaloid stemofoline.
300 $a 201 p.
500 $a Source: Dissertation Abstracts International, Volume: 71-09, Section: B, page: 5470.
500 $a Adviser: Steven M. Weinreb.
502 $a Thesis (Ph.D.)--The Pennsylvania State University, 2010.
520 $a We have developed novel methodology that produced the first examples of intramolecular 1,4-conjugate additions of carbon and hetero nucleophiles to vinylnitroso compounds. Combining several new methods developed in these labs, we have been able to access the requisite precursors and optimize the reaction conditions for these transformations. Namely, we have shown that a vinylnitroso species generated from the corresponding alpha-chlorosilyl-oximes using fluoride ion, interacts with a tethered nucleophile in a 1,4-manner producing a variety of carbocyclic and heterocyclic products. Recognizing that this methodology allows us facile entry into the stemofoline alkaloid skeleton, we have attempted to apply it to an asymmetric total synthesis of this metabolite. In the course of these studies new methodology for oxidation of alpha-hydroxy-beta-ketoesters to alpha-diazo-beta-ketoesters emerged, thus allowing us to generate some of the intermediates required to advance the synthesis.
590 $a School code: 0176.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Polymer. $3 1018428
690 $a 0490
690 $a 0495
710 2 $a The Pennsylvania State University. $3 699896
773 0 $t Dissertation Abstracts International $g 71-09B.
790 1 0 $a Weinreb, Steven M., $e advisor
790 $a 0176
791 $a Ph.D.
792 $a 2010
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3420168