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Enoki, Winter Mushroom · 2005 · Research Support, Non U.S. Gov'T

Medium relevance

Enantioselective Total Synthesis of Enokipodins A–D, Antimicrobial Sesquiterpenes Produced by the Mushroom, Flammulina velutipes

Flammulina velutipes

Immune support
SpeciesEnoki, Winter Mushroom
JournalBioscience, biotechnology, and biochemistry
Year2005

Key points

  • 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

Metadata-grounded summary

Citation abstract

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.

Citation

Saito M, Kuwahara S (2005). Enantioselective Total Synthesis of Enokipodins A–D, Antimicrobial Sesquiterpenes Produced by the Mushroom, Flammulina velutipes. Bioscience, biotechnology, and biochemistry https://doi.org/10.1271/bbb.69.374 PMID: 15725664

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