Improved syntheses of morinol C and D by employing Mizoroki-Heck reaction and their cytotoxic and antimicrobial activities.
Improved syntheses of optically pure (-)- and (+)-morinol C, and (-)- and (+)-morinol D were achieved by employing the Mizoroki-Heck reaction to construct the cinnamyl moiety. The protective group of the alkene substrate affected the yield of this key reaction. The reaction with a combination of the acetate-protected olefin and 4-methoxyphenylboronic acid gave the best result producing morinol C and D. All stereoisomers of morinol C and D showed cytotoxic activity, with (R,R)-morinol C showing the highest antibacterial activity.
Ogura
Koji
K
Faculty of Agriculture, Ehime University, Tarumi, Matsuyama, Ehime, Japan.
Sugahara
Takuya
T
Maruyama
Masafumi
M
Akiyama
Koichi
K
Yamauchi
Satoshi
S
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity
D000890:Anti-Infective Agents; D011714:Pyrans