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Title: Synthesis of the tetrahydropyran fragment of bistramide D
Authors: Bates, Roderick Wayland
Li, Lu
Palani, Kalpana
Phetsang, Wanida
Loh, Joanna Kejun
Keywords: 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.
Journal: Asian journal of organic chemistry
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.
ISSN: 2193-5807
DOI: 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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