Abstract

The isoindolone fragment of cytochalasin D has been assembled by Diels-Alder reaction of an optically active N-benzoyl pyrrolinone intermediate with a substituted diene. This intermediate will be taken on to analogs of cytochalasin D by a ring expansion sequence where a 6-membered sulfide ring is bridged across the alpha, alpha' positions by a 6-carbon chain. The result of this reaction would be to complete the 11-membered carbocyclic periphery of cytochalasin D.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Cancer Institute (NCI)
Type
Research Project (R01)
Project #
5R01CA017918-11
Application #
3164804
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1978-07-01
Project End
1985-12-31
Budget Start
1985-01-01
Budget End
1985-12-31
Support Year
11
Fiscal Year
1985
Total Cost
Indirect Cost

  Institution

Name
University of Wisconsin Madison
Department
Type
Schools of Arts and Sciences
DUNS #
161202122
City
Madison
State
WI
Country
United States
Zip Code
53715

  Publications

Peris, Gorka; Vedejs, Edwin (2015) Enantiocontrolled synthesis of a tetracyclic aminal corresponding to the core subunit of diazonamide A. J Org Chem 80:3050-7
Wiedner, Susan D; Vedejs, Edwin (2012) Reactivity of aziridinomitosene derivatives related to FK317 in the presence of protic nucleophiles. J Org Chem 77:1045-55
Nelson, John M; Vedejs, Edwin (2010) Metalated aziridines for cross-coupling with aryl and alkenyl halides via palladium catalysis. Org Lett 12:5085-7
Duffey, Trisha A; Mackay, James A; Vedejs, Edwin (2010) Catalytic parallel kinetic resolution under homogeneous conditions. J Org Chem 75:4674-85
Wiedner, Susan D; Vedejs, Edwin (2010) Aziridinomitosanes via lactam cyclization. Org Lett 12:4030-3
Duffey, Trisha A; Shaw, Scott A; Vedejs, Edwin (2009) AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates. J Am Chem Soc 131:14-5
Peris, Gorka; Vedejs, Edwin (2008) Diastereoselective carboxyl migrations of 3-arylbenzofuranones. J Org Chem 73:1158-61
Bobeck, Drew R; Warner, Don L; Vedejs, Edwin (2007) Internal azomethine ylide cycloaddition methodology for access to the substitution pattern of aziridinomitosene A. J Org Chem 72:8506-18
Warner, Don L; Hibberd, Amber M; Kalman, Monica et al. (2007) N-silyl protecting groups for labile aziridines: application toward the synthesis of N-H aziridinomitosenes. J Org Chem 72:8519-22
Shaw, Scott A; Aleman, Pedro; Christy, Justin et al. (2006) Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon. J Am Chem Soc 128:925-34

Showing the most recent 10 out of 29 publications