New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

MY Laurent, V Stocker, VM Temgoua, G Dujardin…

Index: Laurent, Mathieu Y.; Stocker, Vivien; Temgoua, Valery Momo; Dujardin, Gilles; Dhal, Robert Tetrahedron Letters, 2011 , vol. 52, # 14 p. 1608 - 1611

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Citation Number: 6

Abstract

A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels– Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans.