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Intermolecular [5+2] cycloadditions :Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Intermolecular [5+2] cycloadditions :
Reminder of title:	Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets.
Author:	Scanio, Marc Julian Charles.
Description:	297 p.
Notes:	Adviser: Paul A. Wender.
Notes:	Source: Dissertation Abstracts International, Volume: 64-03, Section: B, page: 1252.
Contained By:	Dissertation Abstracts International64-03B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3085365
ISBN:	0496331728

Intermolecular [5+2] cycloadditions :Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets.
Scanio, Marc Julian Charles.

Intermolecular [5+2] cycloadditions :Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets. [electronic resource] - 297 p.

Adviser: Paul A. Wender.

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

A novel, serial [5+2]/[4+2] cycloaddition process is reported. This process employs readily available starting materials that are predictably converted into highly functionalized polycyclic products. The serial cycloadditions are readily conducted on a small or preparative scale.

ISBN: 0496331728Subjects--Topical Terms:

193634
Chemistry, Organic.

Intermolecular [5+2] cycloadditions :Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets.
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100 0 $a Scanio, Marc Julian Charles. $3 227010
245 1 0 $a Intermolecular [5+2] cycloadditions : $b Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets. $h [electronic resource]
300 $a 297 p.
500 $a Adviser: Paul A. Wender.
500 $a Source: Dissertation Abstracts International, Volume: 64-03, Section: B, page: 1252.
502 $a Thesis (Ph.D.)--Stanford University, 2003.
520 # $a A novel, serial [5+2]/[4+2] cycloaddition process is reported. This process employs readily available starting materials that are predictably converted into highly functionalized polycyclic products. The serial cycloadditions are readily conducted on a small or preparative scale.
520 # $a An efficient, preparative scale synthesis of 1-(2-methyoxyethoxy)-1-vinylcyclopropane and the investigation of the utility of this reagent as a new five-carbon component in metal-catalyzed [5+2] cycloadditions is reported. A new cycloaddition protocol is also described that proceeds up to 12-fold faster and with 10-fold less catalyst than previously described. This procedure is readily conducted on a small or preparative scale.
520 # $a Cycloaddition reactions are among the most synthetically useful individual processes for rapidly increasing molecular complexity. The Wender group has been involved in designing and developing new transition metal-catalyzed cycloaddition reactions that are theoretically forbidden in the absence of a catalyst or are difficult to achieve. Examples of these include the recent development of rhodium-catalyzed intra- and intermolecular [5+2] cycloadditions. These cycloadditions provide fundamentally new strategies for the synthesis of compounds containing seven-membered rings. In addition to introducing these new reactions, efforts have been made to render them practical and efficient.
520 # $a Finally the first examples of transition metal-catalyzed aza-[5+2] cycloadditions of cyclopropyl imines and alkynes for the synthesis of azepines is described. The reported serial imine formation/aza-[5+2] cycloaddition reactions enable an azepine synthesis from three commercially available starting materials in a single reaction vessel. This reaction has also been explored with a substituted imine, yielding a single regioisomer, and has been demonstrated on a preparative scale.
520 # $a In conclusion, intermolecular [5+2] cycloadditions have been demonstrated to be practical and efficient in the synthesis of seven-membered ring containing compounds.
520 # $a The utility of the intermolecular [5+2] cycloaddition is illustrated by its use in the synthesis of biologically active targets. The rational design of biologically active targets, relying on X-ray structural information and known SAR combined with molecular modeling, is described. The synthesis and biological evaluation of these molecules is also reported.
590 $a School code: 0212.
650 # 0 $a Chemistry, Organic. $3 193634
710 0 # $a Stanford University. $3 212607
773 0 # $g 64-03B. $t Dissertation Abstracts International
790 $a 0212
790 1 0 $a Wender, Paul A., $e advisor
791 $a Ph.D.
792 $a 2003
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