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Total synthesis of welwitindolinone ...

Reisman, Sarah Elizabeth.

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Total synthesis of welwitindolinone A isonitrile.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Total synthesis of welwitindolinone A isonitrile./
作者:	Reisman, Sarah Elizabeth.
面頁冊數:	405 p.
附註:	Adviser: John L. Wood.
Contained By:	Dissertation Abstracts International67-04B.
標題:	Chemistry, Organic. -
電子資源:	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:

516206
Chemistry, Organic.

Total synthesis of welwitindolinone A isonitrile.
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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.
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