A stereoselective synthesis of the C-10 to C-18 (right-half) fragment of mycalamides employing lewis acid promoted intermolecular aldol reaction.
[reaction: see text] Beginning with D-mannitol, a stereoselective synthesis of the right-half segment of the mycalamides has been accomplished by employing Lewis acid catalyzed intermolecular aldol reaction and oxypalladation as the key steps.
Toyota
M
M
Department of Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai, 980-8578, Japan.
Hirota
M
M
Hirano
H
H
Ihara
M
M
D000818:Animals; D002384:Catalysis; D007202:Indicators and Reagents; D008353:Mannitol / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008387:Marine Toxins; D011714:Pyrans; C059647:mycalamide B; C059646:mycalamide A; D008353:Mannitol