Abstract
Formal synthesis of furanodictine B is described starting from
d-glucose.
An efficient formal synthesis of furanodictine B
1b is described starting from
d-glucose. The synthetic protocol is based on deriving the bicyclic intermediate
2 from
d-glucose by a modified method and its further manipulations to obtain the advanced intermediate
8. Methanolysis of compound
2 to the 2-hydroxy derivative
3 followed by its conversion to the corresponding 2-
O-triflate
4 is described. Inversion of configuration at C(2) of compound
4 by nucleophilic displacement with NaN
3 gives the azido derivative
5. Straightforward reactions of azide derivative
5 to the corresponding amine
6,
N-acetyl derivative
7 and to the required template
8 are described. Conversion of
8 to the natural product
1b has previously been reported.