Synthesis of the Tetrahydropyran Fragment of Bistramide D

Roderick W. BatesLu LiKalpana PalaniWanida PhetsangJoanna Kejun LohNanyang Technological UniversityMahidol University2018-11-092018-11-092014-01-01Asian Journal of Organic Chemistry. Vol.3, No.7 (2014), 792-79621935807219358072-s2.0-84903777289https://repository.li.mahidol.ac.th/handle/20.500.14594/33647A synthesis of the tetrahydropyran (THP) moiety of bistramideD 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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.Mahidol UniversityChemistrySynthesis of the Tetrahydropyran Fragment of Bistramide DArticleSCOPUS10.1002/ajoc.201402052