80677-96-9Relevant articles and documents
Three-component coupling via the squarate ester cascade as a concise route to the bioactive triquinane sesquiterpene hypnophilin.
Geng, Feng,Liu, Jian,Paquette, Leo A
, p. 71 - 73 (2007/10/03)
[reaction: see text] A squarate ester cascade is used to provide in one step, via the coupling of three reactants, a highly oxygenated linear triquinane product. The latter is transformed in nine steps into hypnophilin. The access route involves a combination of chlorination, reduction, dehydration, and oxidation maneuvers in the proper sequence.
Chemistry and Stereochemistry of Iridoids, XVI. - EPC-Synthesis of (-)-Hypnophilin
Weinges, Klaus,Iatridou, Helene,Dietz, Uwe
, p. 893 - 902 (2007/10/02)
The synthesis of enantiomerically pure (-)-hypnophilin (27) from (6R,7R)-(-)-7-hydroxy-3-oxabicyclonon-1-en-9-one (1) is described. 1 was obtained in 93 percent yield from catalpol, which is readily available from the aqueous sodium carbonate extra
Intramolecular 1,3-Diyl Trapping Reactions. Total Synthesis of (+/-)-Hypnophilin and (+/-)-Coriolin. Formation of the Trans-Fused Bicyclooctane Ring System
Hijfte, Luc Van,Little, R. Daniel,Petersen, Jeffrey L.,Moeller, Kevin D.
, p. 4647 - 4661 (2007/10/02)
The intramolecular 1,3-diyl trapping reaction served as the key step in total synthesis of (+/-)-coriolin (1) and the first total synthesis of (+/-)-hypnophilin (3).In the process, four of the required eight (coriolin) or six (hypnophilin) stereocenters w