Synthesis of the epimer of pericosine B from (-)-quinic Acid.
Synthesis of the epimer of pericosine B from (-)-quinic acid was achieved. This synthesis involves some regioselective and stereoselective processes. The desired product showed lower cytotoxic activity in comparison with natural pericosine B against the P388 leukemia cell line. The result implies that the stereocenter of C-6 in natural pericosine B plays an important role in this activity.
Usami
Yoshihide
Y
Osaka University of Pharmaceutical Sciences, Takatsuki, Osaka 569-1094, Japan. usami@gly.oups.ac.jp
Hatsuno
Chikage
C
Yamamoto
Hiroe
H
Tanabe
Manabu
M
Numata
Atsushi
A
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D045744:Cell Line, Tumor; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D011801:Quinic Acid / Q000737:chemistry*; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000970:Antineoplastic Agents; C496389:pericosine B; D011801:Quinic Acid; D012765:Shikimic Acid