Enantioselective total synthesis of enokipodins A-D, antimicrobial sesquiterpenes produced by the mushroom, Flammulina velutipes.
The first enantioselective total synthesis of enokipodins A, B, C and D, highly oxidized alpha-cuparenone-type sesquiterpenoids possessing antimicrobial activity, was accomplished in 8-28% overall yields from methyl (2,5-dimethoxy-4-methylphenyl)acetate by applying Meyers' diastereoselective alkylation protocol for the construction of their C7-quaternary asymmetric center. The present synthesis confirmed the absolute configuration of the enokipodins, and also constitutes a formal enantioselective synthesis of (S)-1,4-cuparenediol and (S)-cuparene-1,4-quinone.
Saito
Mana
M
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Kuwahara
Shigefumi
S
D000363:Agaricales / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000890:Anti-Infective Agents; D012717:Sesquiterpenes