Total syntheses of enokipodins A and B utilizing palladium-catalyzed addition of an arylboronic acid to an allene.
The enantioselective total syntheses of enokipodins A and B, alpha-cuparenone-type sesquiterpenoids with antimicrobial activity, have been achieved. The key step is the enantiospecific construction of the quaternary carbon center using a palladium-catalyzed addition of an arylboronic acid to an allene followed by an Eschenmoser-Claisen rearrangement.
Yoshida
Masahiro
M
Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima, 770-8505, Japan. yoshida@ph.tokushima-u.ac.jp
Shoji
Yasunobu
Y
Shishido
Kozo
K
D000466:Alkadienes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000466:Alkadienes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001688:Biological Products; D001897:Boronic Acids; D012717:Sesquiterpenes; C539533:enokipodin A; C539534:enokipodin B; C025947:propadiene; D010165:Palladium