Tetrahedron

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

Index: Sturino, Claudio F.; Doussot, Pascale; Paquette, Leo A. Tetrahedron, 1997 , vol. 53, # 26 p. 8913 - 8926

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Citation Number: 21

Abstract

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 ...