Tetrahedron letters

A formal synthesis of the syributins and secosyrins and a synthetic approach towards the syringolides

M Carda, E Castillo, S Rodri, E Falomir, JA Marco

Index: Carda, Miguel; Castillo; Rodriguez; Falomir; Marco, J. Alberto Tetrahedron Letters, 1998 , vol. 39, # 48 p. 8895 - 8896

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Citation Number: 24

Abstract

The indium-mediated allylation of a protected derivative ofd-xylulose in aqueous THF is highly diastereoselective. The obtained product has been converted in four steps into a spiro lactone previously transformed into syributins and secosyrins. This remarkably short reaction sequence constitutes therefore a formal synthesis of these compounds and provides also a promising synthetic approach towards the syringolides.

~74%

First total synthesis of (+)-secosyrin 1

[Mukai, Chisato; Moharram, Sameh M.; Hanaoka, Miyoji Tetrahedron Letters, 1997 , vol. 38, # 14 p. 2511 - 2512]