PMID: 11902886Mar 21, 2002Paper

Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues

Journal of the American Chemical Society
Jack D Scott, Robert M Williams

Abstract

The first total synthesis of the potent antitumor antibiotic (-)-tetrazomine has been accomplished. A new method for the formation of the allylic amine precursor to an azomethine ylide has been developed and exploited in an efficient [1,3]-dipolar cycloaddition to afford the key tetracyclic intermediate used in the synthesis of (-)-tetrazomine. Several analogues of tetrazomine have been synthesized and tested for antimicrobial and biochemical activity.

Citations

May 10, 2005·Amino Acids·C Kadouri-Puchot, S Comesse
Aug 9, 2008·The Journal of Organic Chemistry·Dan Fishlock, Robert M Williams
Oct 7, 2016·The Journal of Organic Chemistry·Vanaparthi SatheeshTharmalingam Punniyamurthy
May 7, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yi Chiao Fan, Ohyun Kwon
Nov 27, 2018·Chemistry : a European Journal·Vladimir AkhmetovKonstantin Amsharov
Mar 28, 2007·Angewandte Chemie·Guillaume Vincent, Robert M Williams
Feb 26, 2009·Natural Product Reports·Carmen Cuevas, Andrés Francesch
Jun 10, 2010·Chemistry : a European Journal·Carmen Avendaño, Elena de la Cuesta
Jun 28, 2003·Natural Product Reports·Kenneth W Bentley
Dec 10, 2020·Organic & Biomolecular Chemistry·Shuang YangZhenhua Ding
May 6, 2008·Journal of the American Chemical Society·Yan-Chao WuJieping Zhu
May 9, 2002·Chemical Reviews·Jack D Scott, Robert M Williams
Oct 12, 2018·Chemical Reviews·Shaojian TangJason J Chruma
Dec 5, 2003·Journal of the American Chemical Society·Eric R AshleyBrian M Stoltz

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