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A Rapid Stereocontrolled Entry to the ABCD Tetracyclic Core of Neotuberostemonine

2003; Wiley; Volume: 42; Issue: 14 Linguagem: Inglês

10.1002/anie.200250507

1521-3773

Kevin I. Booker‐Milburn, Paul R. Hirst, J.P.H. Charmant, Luke H. J. Taylor,

Chemical synthesis and alkaloids

Angewandte Chemie International EditionVolume 42, Issue 14 p. 1642-1644 Communication A Rapid Stereocontrolled Entry to the ABCD Tetracyclic Core of Neotuberostemonine† Kevin I. Booker-Milburn Dr., Kevin I. Booker-Milburn Dr. k.booker-milburn@bristol.ac.uk School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK, Fax: (+44) 117-929-8611Search for more papers by this authorPaul Hirst Dr., Paul Hirst Dr. School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK, Fax: (+44) 117-929-8611Search for more papers by this authorJonathan P. H. Charmant Dr., Jonathan P. H. Charmant Dr. Structural Chemistry Laboratory, School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UKSearch for more papers by this authorLuke H. J. Taylor, Luke H. J. Taylor Structural Chemistry Laboratory, School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UKSearch for more papers by this author Kevin I. Booker-Milburn Dr., Kevin I. Booker-Milburn Dr. k.booker-milburn@bristol.ac.uk School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK, Fax: (+44) 117-929-8611Search for more papers by this authorPaul Hirst Dr., Paul Hirst Dr. School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK, Fax: (+44) 117-929-8611Search for more papers by this authorJonathan P. H. Charmant Dr., Jonathan P. H. Charmant Dr. Structural Chemistry Laboratory, School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UKSearch for more papers by this authorLuke H. J. Taylor, Luke H. J. Taylor Structural Chemistry Laboratory, School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UKSearch for more papers by this author First published: 10 April 2003 https://doi.org/10.1002/anie.200250507Citations: 24 † This work was supported by a grant (GR/R02382/01) from the Engineering and Physical Sciences Research Council (EPSRC). Read the full textAboutPDF 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 Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z50507_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume42, Issue14April 11, 2003Pages 1642-1644 RelatedInformation