PMID: 11325279Apr 28, 2001Paper

Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine

The Journal of Organic Chemistry
P Wipf, C R Hopkins

Abstract

The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel--Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.

References

Dec 1, 1991·The Journal of Antibiotics·T SatoH Kaniwa
Sep 13, 1967·Journal of the American Chemical Society·G W AndersonF M Callahan
Aug 1, 1994·The Journal of Antibiotics·T HidaS Harada
Apr 5, 1994·Biochemistry·R M WilliamsT N Tippie
Mar 31, 1999·Proceedings of the National Academy of Sciences of the United States of America·E J MartinezE J Corey
Oct 25, 2001·The Journal of Organic Chemistry·Peter Wipf, Corey R. Hopkins

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Citations

Aug 25, 2011·Chemical Communications : Chem Comm·Laura H S SmithDavid J Procter
Aug 3, 2010·Chemistry, an Asian Journal·Sasiwadee Boonya-UdtayanNopporn Thasana
May 6, 2008·Journal of the American Chemical Society·Yan-Chao WuJieping Zhu
May 9, 2002·Chemical Reviews·Jack D Scott, Robert M Williams
Jul 15, 2004·Chemical Reviews·Maria Chrzanowska, Maria D Rozwadowska
Sep 17, 2010·The Journal of Organic Chemistry·William H MilesApril J Thrall
Feb 22, 2002·The Journal of Organic Chemistry·Ralph Nicholas SalvatoreKyung Woon Jung

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