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Enoki, Winter Mushroom · 2014 · Research Support, Non U.S. Gov'T

Medium relevance

Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes.

Flammulina velutipes

Oncology
SpeciesEnoki, Winter Mushroom
JournalOrganic & biomolecular chemistry
Year2014

Key points

  • The first total synthesis of a norsesquiterpene alkaloid (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, isolated from the mushroom-forming fungus Flammulina velutipes, in both racemic and enantiomeric pure forms, is reported
  • The (-)-enantiomer of the natural product has been synthesized from the D-(-)-pantolactone chiral pool
  • The synthesis features a one-pot, three-step reaction sequence comprising an enyne RCM/Diels-Alder/aromatization to construct the desired indane skeleton present in the natural product
  • Our synthesis further confirms the assigned structure and absolute configuration of the natural product

Metadata-grounded summary

Citation abstract

The first total synthesis of a norsesquiterpene alkaloid (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, isolated from the mushroom-forming fungus Flammulina velutipes, in both racemic and enantiomeric pure forms, is reported. The (-)-enantiomer of the natural product has been synthesized from the D-(-)-pantolactone chiral pool. The synthesis features a one-pot, three-step reaction sequence comprising an enyne RCM/Diels-Alder/aromatization to construct the desired indane skeleton present in the natural product. Our synthesis further confirms the assigned structure and absolute configuration of the natural product.

Citation

Kashinath K, Jadhav PD, Reddy DS (2014). Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes. Organic & biomolecular chemistry https://doi.org/10.1039/c4ob00300d PMID: 24769797

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