Guo H, O'Doherty GA De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction Angewandte Chemie, International Edition46(27) (2007)
5206-5208
The structure was elucidated in this paper NCBI PubMed ID:17534991 Journal NLM ID:0370543 Publisher: Weinheim: Wiley-VCH Correspondence: george.odohertymail.wvu.edu Institutions: Department of Chemistry, West Virginia University, 217 Clark Hall, P.O. 6045, Morgantown, WV 26506, USA
A highly enantioselective and stereocontrolled approach to d-, l- and 8-epi-d-swainsonine has been developed from achiral furan and γ-butyrolactone. A one-pot hydrogenolysis of both azide and benzyl ether followed by an intramolecular reductive amination has been employed as key step to establish the indolizidine ring system. The absolute stereochemistry was installed by the Noyori reduction and the relative stereochemistry by the use of several highly diastereoselective palladium catalyzed glycosylation, Luche reduction, dihydroxylation and palladium catalyzed azide allylation reactions. This practical approach provide multigram quantities of indolizidine natural product d-swainsonine in 13 steps and 25% overall yield.
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