Strategies for the Synthesis of Ellagitannins - Chemistry and Biology of Ellagitannins - page 196

glucopyranose, and the unnatural 1,2,3,4,6-penta- O -galloyl-α- D -glucopyranose,
Tetrahedron , 53, pp. 10725-10732.
Khanbabaee, K. and Lötzerich, K. (1997b). The first total synthesis of praecoxin B and
pterocarinin C, two natural products of the tannin class, Liebigs Ann.
Chem./Recueil , pp. 1571-1575. NB: the structure of the compound named
“pterocarinin C” in this article corresponds to the structure of “pterocaryarin C”,
thus renamed in 1989, probably to avoid confusion with the C -glycosidic
pterocarinins A and B (see Nonaka et al. , 1989a), by Nishioka and collaborators
who first isolated and characterized this β-1,4,6-trigalloyl-2,3-( S )-
hexahydroxydiphenoylglucopyranose compound (see Saijo et al. , 1989).
Unfortunately, the use of the original name has persisted in the literature.
Khanbabaee, K., Schulz, C. and Lötzerich, K. (1997). Synthesis of enantiomerically pure
strictinin using a stereoselective esterification reaction, Tetrahedron Lett. , 38, pp.
1367-1368.
Khanbabaee, K. and Lötzerich, K. (1998). Synthesis of enantiomerically pure unusual
ellagitannins 1,4,6-tri- O -galloyl-2,3-( R )-hexahydroxydiphenoyl-β- D -gluco-
pyranoside and 4,6-Di- O -galloyl-2,3-( R )-hexahydroxydiphenoyl- D -glucoside. The
proposed chemical structures for cercidinin A and B must be revised, J. Org.
Chem. , 63, pp. 8723-8728.
Khanbabaee, K. and Lötzerich, K. (1999). Studies relevant to ellagitannin chemistry:
strain-energy induced opening of the D -Glucono-δ-lactone ring of an ellagitannin
derivative and the synthesis of ellagitannin natural products with a D -gluconic acid
moiety, Eur. J. Org. Chem. , pp. 3079-3083.
Khanbabaee, K., Lötzerich, K., Borges, M. and Großer, M. (1999). The first total
syntheses of enantiomerically pure naturally occurring ellagitannins gemin D and
its regioisomer hippomanin A, J. Prakt. Chem. , 341, pp. 159-166.
Khanbabaee, K. and van Ree, T. (2001a). Tannins: classification and definition, Nat.
Prod. Rep. , 18, pp. 641-649.
Khanbabaee, K. and van Ree, T. (2001b). Strategies for the synthesis of ellagitannins,
Synthesis , pp. 1585-1610.
Khanbabaee, K. and Großer, M. (2003). An efficient total synthesis of pedunculagin by
using a twofold intramolecular double esterification strategy, Eur. J. Org. Chem. ,
pp. 2128-2131.
Kida, T., Masuyama, A. and Okahara, M. (1990). Preparation of trihydroxycarboxylates
bearing a long-chain alkyl acetal group from glucono-1,5-lactone, Tetrahedron
Lett. , 31, pp. 5939-5942.
Königs, W. and Knorr, E. (1901). Ueber einige Derivate des Traubenzuckers und der
Galactose, Chem. Ber. , 34, pp. 957-981.
Kuzuhara, H. and Fletcher, H. G. (1967). Syntheses with partially benzylated sugars.
VIII. Substitution at carbon-5 in aldose. The synthesis of 5- O -methyl- D -
glucofuranose derivatives, J. Org. Chem. , 32, pp. 2531-2534.
Lee, S. H., Tanaka, T., Nonaka, G. and Nishioka, I. (1989). Sedoheptulose digallate from
Cornus officinalis , Phytochemistry , 28, pp. 3469-3472.
Lehmann, J. (1996). Kohlenhydrate - Chemie und Biologie , second edition, Georg
Thieme-Verlag: Stuttgart.