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Abstract

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Paper | Special issue | Vol 84, No. 1, 2012, pp. 597 - 613
Published online: 7th July, 2011
DOI: 10.3987/COM-11-S(P)29
Synthesis of Fused Tricyclic Heterocycles by Condensation, Cyclization, Dipolar Cycloaddition Cascade of α-Benzenesulfonyl and α-Phenylthio Substituted Aldehydes

Iain Coldham,* Adam J. M. Burrell, Luke Watson, Niall Oram, and Nathaniel G. Martin

*Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, U.K.

Abstract

Heating α-benzenesulfonyl- or α-phenylthio-aldehydes that contain a tethered alkyl chloride and alkene originating from the α- position of the aldehyde with hydroxylamine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate oxime, then cyclization to an intermediate nitrone, then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete stereochemical control and were converted in two steps either to the natural product (±)-myrioxazine A or to a 1,3-oxazine that is present in some yuzurimine type Daphniphyllum alkaloids.

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