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. 2010 Nov 19;12(22):5226-9.
doi: 10.1021/ol102525w. Epub 2010 Oct 28.

Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides

Stéphanie M Guéret  1 , Daniel P Furkert, Margaret A Brimble
Affiliations

Synthesis of a functionalized 7,6-bicyclic spiroimine ring fragment of the spirolides

Stéphanie M Guéret et al. Org Lett. .

Abstract

The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

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