A FORMAL TOTAL SYNTHESIS OF BIOXALOMYCIN BETA 2

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Title:	A FORMAL TOTAL SYNTHESIS OF BIOXALOMYCIN BETA 2
Author:	KANISKAN, H. ÜMIT
Description:	A new cycloadditive approach for the asymmetric synthesis of the bioxalomycin family of antitumor antibiotics has been developed. Through this new synthetic route, a formal total synthesis of (+)-cyanocycline A and bioxalomycin beta 2 was accomplished and an effective approach to the other members of this family has been demonstrated. The key step of this synthetic route involves a Ag(I)-catalyzed asymmetric multicomponent [C+NC+CC] synthesis of the highly functionalized pyrrolidine core of bioxalomycin beta 2, utilizing Oppolzer’s chiral glycylsultam as a chiral auxiliary. With this new multicomponent reaction, the desired pyrrolidine 323, possessing the 5 of 8 stereocenters present in the target molecule, was obtained efficiently. This new multicomponent [C+NC+CC] cascade also provided enantiomerically enriched pyrrolidines which were unavailable via existing 1,3-dipolar cycloaddition technology. A variety of aliphatic and aromatic aldehydes was used to demonstrate the generality of this new methodology for the synthesis of highly functionalized pyrrolidines.
Permanent Link:	http://rave.ohiolink.edu/etdc/view?acc_num=case1180451443 http://hdl.handle.net/2374.OX/17293
Date:	2007

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