56881-48-2Relevant articles and documents
Furanosesquiterpenoids: Total Synthesis of Pallescensins 2, F, and G
Matsumoto, Takashi,Usui, Shuji
, p. 491 - 493 (2007/10/02)
Oxidation of the synthetic pallescensin 1 with m-chloroperbenzoic acid, follwed by treatment of the resulting epoxide with lithium diethylamide, afforded 3--4,4-dimethyl-2-methylenecyclohexanol (6).The alcohol 6 was dehydrated with refluxing hexamethylphosphoric triamide to give pallescensin 2.Oxidation of 6 with pyridinium chlorochromate, followed by intramolecular cyclization with 85percent phosphoric acid, afforded 5,5a,6,7,8,9,9a,10-octahydro-6,6-dimethyl-4H-benzocycloheptafuran-9-one.This was converted into the corresponding α,β-unsaturated ketone (10) via an α-phenylseleno ketone.Reduction of 10 with lithium aluminium hydride, followed by dehydration with hexamethylphosphoric triamide at 200-210 deg C, afforded pallescensin G, which was further isomerized to pallescensin F.