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Stereocontrolled Total Synthesis of (+)‐Leucascandrolide A

2003; Wiley; Volume: 42; Issue: 3 Linguagem: Inglês

10.1002/anie.200390112

1521-3773

Ian Paterson, Matthew T. Tudge,

Traditional and Medicinal Uses of Annonaceae

Angewandte Chemie International EditionVolume 42, Issue 3 p. 343-347 Communication Stereocontrolled Total Synthesis of (+)-Leucascandrolide A† Ian Paterson Prof., Ian Paterson Prof. [email protected] University Chemical Laboratory Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362Search for more papers by this authorMatthew Tudge, Matthew Tudge University Chemical Laboratory Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362Search for more papers by this author Ian Paterson Prof., Ian Paterson Prof. [email protected] University Chemical Laboratory Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362Search for more papers by this authorMatthew Tudge, Matthew Tudge University Chemical Laboratory Lensfield Road, Cambridge, CB2 1EW, UK, Fax: (+44) 1223-336-362Search for more papers by this author First published: 20 January 2003 https://doi.org/10.1002/anie.200390112Citations: 89 † We thank the EPSRC (studentship to M.T. and GR/N08520), the EU (Network HPRN-CT-2000-00018), and Merck, Pfizer, and Novartis for support. 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 Graphical Abstract Apparently no longer available from its natural source is the potent cytotoxic and antifungal agent leucascandrolide A (1), which was initially isolated from a New Caledonian calcareous sponge. A highly stereocontrolled total synthesis of this structurally unique macrolide commences with a Jacobsen asymmetric hetero Diels–Alder reaction to configure the tetrahydropyran ring. An efficient endgame relies on two Mitsunobu reactions, the first to generate the 18-membered macrolactone and the second to attach the oxazole-bearing side chain. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z50143_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, Issue3January 20, 2003Pages 343-347 RelatedInformation