Beilstein J. Org. Chem.2014,10, 213–223, doi:10.3762/bjoc.10.17
in natural products, in particular as toxins in marine organisms or plants [6][7]. A few reports in the literature deal with seven-membered polyhydroxylated ethers like septanosides (containing an anomeric center) [8] as well as compounds without an acetal moiety. Known methods for the construction
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Graphical Abstract
Scheme 1:
General approach to enantiopure the poly(hydroxy)aminopyrans D (n = 0) and the aminooxepanes D (n =...
Beilstein J. Org. Chem.2012,8, 522–527, doi:10.3762/bjoc.8.59
Supriya Dey Narayanaswamy Jayaraman Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India 10.3762/bjoc.8.59 Abstract This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a
acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl
septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C
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Graphical Abstract
Figure 1:
Synthetic route to transform oxyglycal I to a septanoside V.