Synthesis of polycyclic structures by Diels-Alder reaction of inner-outer-ring 1,3-bis[(trimethylsilyl)oxy]dienes.

Pérez Sestelo, J.; Real, M. M.; Mouriño, A.; Sarandeses, L. A.

Abstract

Tetrahedron Lett. 1999, 40, 985–988 (DOI: 10.1016/S0040-4039(98)02463-0).

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In this paper we describe regioselective one-pot preparations of inner-outer-ring 
1,3-bis[trimethylsilyloxy]dienes and their Diels-Alder reactions with electron-deficient dienophiles. The dienes were prepared in quantitative yield, and the Diels-Alder reactions proceeded smoothly, regioselectively and with good yields, allowing efficient construction of highly functionalized polycyclic skeletons such as naphthofurans, benzofurans and various carbocycles present in natural and non-natural products.