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|Title:||Synthesis of the tetrahydropyran fragment of bistramide D||Authors:||Bates, Roderick W.
Loh, Joanna Kejun
|Keywords:||DRNTU::Science::Chemistry::Organic chemistry||Issue Date:||2014||Source:||Bates, R. W., Li, L., Palani, K., Phetsang, W., & Loh, J. K. (2014). Synthesis of the tetrahydropyran fragment of bistramide D. Asian journal of organic chemistry, 3(7), 792-796.||Series/Report no.:||Asian journal of organic chemistry||Abstract:||A synthesis of the tetrahydropyran (THP) moiety of bistramide D has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.||URI:||https://hdl.handle.net/10356/101581
|ISSN:||2193-5807||DOI:||http://dx.doi.org/10.1002/ajoc.201402052||Rights:||© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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