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Title:Development of a Diastereoselective [4+2]-Annulation of Vinyl Carbodiimides With Chiral N-Alkyl Imines and Its Application to the Synthesis of the Batzelladine Alkaloids: Total Synthesis of (+)-Batzelladine a and (-)-Batzelladine D
Author(s):Arnold, Michael A.
Doctoral Committee Chair(s):Gin, David Y.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich anti-fused polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as a long-range directed hydrogenation and a diastereoselective intramolecular iodoamination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol. Overall, a 13 step asymmetric synthesis of -(-)batzelladine D was accomplished in 7.4% yield, and a 20 step asymmetric synthesis of (+)-batzelladine A was completed in 2.0% yield. Investigations into the application of the imine/vinyl carbodiimide [4+2]-annulation to the syn-fused tricyclic guanidine cores of the batzelladines are also described.
Issue Date:2007
Type:Text
Language:English
Description:207 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2007.
URI:http://hdl.handle.net/2142/84270
Other Identifier(s):(MiAaPQ)AAI3290168
Date Available in IDEALS:2015-09-25
Date Deposited:2007


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