1.
J Org Chem
; 61(11): 3700-3705, 1996 May 31.
Article
in English
| MEDLINE
| ID: mdl-11667218
ABSTRACT
Total synthesis of trideca-O-methyl-alpha-pedunculagin was achieved by a simple sequence. The key step is the synthesis of methyl 4,6-O-benzylidene-2,3-O-[(S)-4,4',5,5',6,6'-hexamethoxydiphenoyl]-alpha-D-glucopyranoside through intramolecular ester-cyclization of racemic hexamethoxydiphenoyl chloride with methyl 4,6-O-benzylidene-alpha-D-glucopyranoside at the 2,3-position. The diastereoselectivity results obtained in the intramolecular cyclization of hexamethoxydiphenic acid to the carbohydrate core raises a very interesting point in considering the pathway of (R)-diphenic acid biosynthesis.