Antimicrobial algal metabolites of unusual structure. Concise synthesis of the highly oxygenated [4.4] spirononene dimethyl gloiosiphone a by ring expansion of …
CF Sturino, P Doussot, LA Paquette
文献索引：Sturino, Claudio F.; Doussot, Pascale; Paquette, Leo A. Tetrahedron, 1997 , vol. 53, # 26 p. 8913 - 8926
A synthesis of dimethyl gloiosiphone A (2) has been realized. The key step involves the boron trifluoride-catalyzed eliminative ring expansion of a 2′-(dimethoxymethyl)-1′- (cyclopenten-1′-yl)-4-hydroxy-2-cyclobuten-1-one, which was directly assembled by condensation of the appropriate cycloalkenyllithium with dimethyl squarate. Following arrival at spirocyclic diketone 17 in only two steps, the cyclopentenedione A-ring was subjected ...
