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Paper | Special issue | Vol 70, No. 1, 2006, pp.367-388
Published online, 21st November, 2006
DOI: 10.3987/COM-06-S(W)36
Cycloaddition Reactions of Amino-Acid Derived Cross-Conjugated Trienes: Stereoselective Synthesis of Novel Heterocyclic Scaffolds

Branko Mitasev, Bingli Yan, and Kay M. Brummond*

*Department of Chemistry, University of Pittsburgh, Parkman Avenue & University Drive, Pittsburgh, PA 15260, U.S.A.

Abstract

Cross-conjugated trienes obtained via a Rh(I)-catalyzed allenic Alder-ene reaction represent a new class of compounds. The synthesis of heterocyclic compounds containing multiple fused rings was accomplished via sequential Diels-Alder reactions of amino-acid derived cross-conjugated trienes. Newly synthesized imino-oxazolidinone fused trienes were used to control the stereoselectivity in an intermolecular cycloaddition sequence. Additionally, intramolecular cycloaddition of ester tethered tetraene stereoselectively afforded fused tricyclic pyridino-pyranone which was effectively utilized in subsequent cycloaddition reactions.