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Total synthesis of welwitindolinone ...

Reisman, Sarah Elizabeth.

Total synthesis of welwitindolinone A isonitrile.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Total synthesis of welwitindolinone A isonitrile.
Author:	Reisman, Sarah Elizabeth.
Description:	405 p.
Notes:	Adviser: John L. Wood.
Notes:	Source: Dissertation Abstracts International, Volume: 67-04, Section: B, page: 2010.
Contained By:	Dissertation Abstracts International67-04B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3214278
ISBN:	9780542652912

Total synthesis of welwitindolinone A isonitrile.
Reisman, Sarah Elizabeth.

Total synthesis of welwitindolinone A isonitrile. - 405 p.

Adviser: John L. Wood.

Thesis (Ph.D.)--Yale University, 2006.

An efficient and highly stereoselective total synthesis of the alkaloid natural product (+/-)-welwitindolinone A isonitrile ( 1) is presented herein. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition reaction. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with complete stereocontrol utilizing a chloronium-ion mediated semi-pinacol rearrangement. In the key step, the natural product (1) was produced from an isocyano-isocyanate precursor using a novel anionic cyclization that simultaneously constructed the spiro-oxindole and vinyl isonitrile moieties. This total synthesis also resulted in the discovery of a SmI2/LiCl-mediated reductive cyclization of tethered alpha,beta-unsaturated ketones and aryl isocyanates to give spiro-oxindoles. While this method was not utilized in the successful total synthesis of 1, it was used to synthesize a variety of functionalized spiro-cyclobutane oxindoles in good yields under mild conditions.

ISBN: 9780542652912Subjects--Topical Terms:

193634
Chemistry, Organic.

Total synthesis of welwitindolinone A isonitrile.
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040 $a UMI $c UMI
100 0 $a Reisman, Sarah Elizabeth. $3 264084
245 1 0 $a Total synthesis of welwitindolinone A isonitrile.
300 $a 405 p.
500 $a Adviser: John L. Wood.
500 $a Source: Dissertation Abstracts International, Volume: 67-04, Section: B, page: 2010.
502 $a Thesis (Ph.D.)--Yale University, 2006.
520 # $a An efficient and highly stereoselective total synthesis of the alkaloid natural product (+/-)-welwitindolinone A isonitrile ( 1) is presented herein. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition reaction. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with complete stereocontrol utilizing a chloronium-ion mediated semi-pinacol rearrangement. In the key step, the natural product (1) was produced from an isocyano-isocyanate precursor using a novel anionic cyclization that simultaneously constructed the spiro-oxindole and vinyl isonitrile moieties. This total synthesis also resulted in the discovery of a SmI2/LiCl-mediated reductive cyclization of tethered alpha,beta-unsaturated ketones and aryl isocyanates to give spiro-oxindoles. While this method was not utilized in the successful total synthesis of 1, it was used to synthesize a variety of functionalized spiro-cyclobutane oxindoles in good yields under mild conditions.
590 $a School code: 0265.
650 # 0 $a Chemistry, Organic. $3 193634
650 # 0 $a Chemistry, Pharmaceutical. $3 206042
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773 0 # $g 67-04B. $t Dissertation Abstracts International
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790 1 0 $a Wood, John L., $e advisor
791 $a Ph.D.
792 $a 2006
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