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Synthesis 2012; 44(23): 3609-3612
DOI: 10.1055/s-0032-1317506
DOI: 10.1055/s-0032-1317506
paper
Stereochemically Reliable Syntheses of Pachastrissamine and Its 2-epi-Congener via Oxazolidinone Precursors from an Established Starting Material N-tert-Butoxycarbonyl-Protected Phytosphingosine
Further Information
Publication History
Received: 04 August 2012
Accepted after revision: 06 October 2012
Publication Date:
05 November 2012 (online)
Abstract
Efficient, stereochemically unambiguous, total syntheses of pachastrissamine and its 2-epi-congener from the readily available common precursor (1R)-1-{(4S,5S)-2-oxo-4-[(trityloxy)methyl]-1,3-oxazolidin-5-yl}pentadecyl methanesulfonate are reported. Syntheses of (3aS,6R,6aR)- and (3aS,6S,6aR)-6-tetradecylhexahydro-2H-cyclopenta[d][1,3]oxazol-2-one by this route have unambiguously resolved a dispute over the structures of these products.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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