2008

TerpenesU 0200 A Domino-Based Approach Toward Stereodefined Heavily Functionalized Cyclo-

hexanes: Synthesis of Iridal's Core Structure. — Key feature of the synthesis of the iridal terpenoid core structures, e.g. (VII)/(VIII), is the Pb(O-Ac)4-mediated domino ring expansion reaction of polyfunctionalized indanol derivatives like (III) or (XIII). The method proceeds under conventional conditions at room temperature for ca. 15 hours or under microwave irradiation for 15 minutes. The installation of the second quaternary stereocenter prior to oxidative ring expansion proceeds with total facial selectivity in the alkylation of hydrindenediol derivatives like (I). — (CORBU, A.; GAURON, G.; CASTRO, J. M.; DAKIR, M.; ARSENIYADIS*, S.; Org. Lett. 9 (2007) 23, 4745-4748; Inst. Chim. Subst. Nat., CNRS, F-91198 Gif-sur-Yvette, Fr.; Eng.) — Mischke

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2008