Studies on the synthesis of myriaporones: stereoselective synthesis of the C5-C13 fragment starting from D-glucose via regioselective reductive opening of methoxybenzylidene acetal.
A stereoselective synthesis is described of the C5-C13 fragment (4) of myriaporone 4 (1) starting from D-glucose by a coupling of the C5-C9 aldehyde (5), prepared using a regioselective reductive ring-opening of methoxybenzylidene acetal, with the C10-C13 iodoolefin (6).
Zheng
B Z
BZ
Department of Chemistry, Okayama University of Science, Japan.
Yamauchi
M
M
Dei
H
H
Yonemitsu
O
O
D001597:Benzylidene Compounds / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D005947:Glucose; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D001597:Benzylidene Compounds; D004852:Epoxy Compounds; D008387:Marine Toxins; D005947:Glucose