Total synthesis of an anticancer norsesquiterpene alkaloid isolated from the fungus Flammulina velutipes.
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.
CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. HomiBhabha Road, Pune, 411008, India. ds.reddy@ncl.res.in.
K
K
Kashinath
Prakash D
PD
Jadhav
D Srinivasa
DS
Reddy
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D055393:Flammulina / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
C000597291:8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta(e)isoindole-1,3(2H,6H)-dione; D000470:Alkaloids; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D010797:Phthalimides