In:
Chemistry – A European Journal, Wiley, Vol. 19, No. 23 ( 2013-06-03), p. 7423-7436
Abstract:
A total synthesis of the proposed structures of fulicineroside and its aglycone fulicinerine is reported. The tetrasubstituted dibenzofuran substructure was accessible either through a Pd‐mediated ortho ‐metalation or by an Ir‐catalyzed meta ‐borylation. The synthesis of the β,β,α‐linked trisaccharide consisting of D ‐olivose, L ‐rhodinose, and L ‐rhamnose was challenged by the unprecedented β‐linked rhodinose. A Pd‐catalyzed β‐selective glycosylation of a 4‐ epi ‐rhodinose and a subsequent Mitsunobu inversion provided selectively the β‐linked L ‐rhodinose‐ L ‐rhamnose disaccharide. Comparison with the reported data for the natural product and the aglycone suggests a misassignment of the structure of the natural product.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.201204545
Language:
English
Publisher:
Wiley
Publication Date:
2013
detail.hit.zdb_id:
1478547-X
detail.hit.zdb_id:
1231884-X
Permalink