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Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF‐Bis(pyran) Subunit

1997; Wiley; Volume: 36; Issue: 24 Linguagem: Inglês

10.1002/anie.199727411

1521-3773

David A. Evans, B. Wesley Trotter, Bernard Côté, Paul J. Coleman,

Chemical synthesis and alkaloids

Angewandte Chemie International Edition in EnglishVolume 36, Issue 24 p. 2741-2744 Communication Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF-Bis(pyran) Subunit†‡ Prof. David A. Evans, Corresponding Author Prof. David A. Evans Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorB. Wesley Trotter, B. Wesley Trotter Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorDr. Bernard Cǒté, Dr. Bernard Cǒté Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorDr. Paul J. Coleman, Dr. Paul J. Coleman Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this author Prof. David A. Evans, Corresponding Author Prof. David A. Evans Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorB. Wesley Trotter, B. Wesley Trotter Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorDr. Bernard Cǒté, Dr. Bernard Cǒté Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this authorDr. Paul J. Coleman, Dr. Paul J. Coleman Department of Chemistry & Chemical Biology, Harvard University, Cambridge, MA 02138 (USA), Fax: Int. code + (617) 495–1460, e-mail: [email protected]Search for more papers by this author First published: January 7, 1997 https://doi.org/10.1002/anie.199727411Citations: 96 † Financial support has been provided by the National Institutes of Health (NIH) and the National Science Foundation (NSF). The NIH BRS Shared Instrumentation Grant Program 1-S10-RR04870 and the NSF (CHE 88-14019) are acknowledged for providing NMR facilities. ‡ Dedicated to Professor Dieter Seebach and Professor Yoshito Kishi on the occasion of their 60th birthdays AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract The first total synthesis of a spongipyran macrolide, altohyrtin C (spongistatin 2; see picture below), has been realized. The spongipyrans derived from marine sponges are among the most potent cytotoxic compounds yet isolated, and exhibit subnanomolar activities against a variety of human cancer cell lines. While the structures proposed for the independently isolated altohyrtins and spongistatins are largely homologous, they differ significantly with regard to internal stereochemical relationships. This discrepancy has been resolved by the total synthesis, which verifies the altohyrtin structural assignment and establishes the identity of altohyrtin C and the independently isolated spongistatin 2. Citing Literature Volume36, Issue24January 7, 1997Pages 2741-2744 RelatedInformation