Hetero Diels-Alder Reactions with Nitroso Dienophiles: Application to the Synthesis of Natural Product Derivatives

Abstract

Hetero Diels-Alder (HDA) reactions with nitroso dienophiles R-N=O are reviewed within the scope of natural product synthesis. These cycloadditions often represent the pivotal reaction step of a total synthesis, because of their high stereo- and regioselective outcome; also because of the introduction of multifunctionality as a direct consequence of the HDA cycloaddition. Asymmetric total syntheses are particularly emphasised using chiral dienes or chiral nitroso dienophiles. 1. Introduction 2. Nitroso Dienophiles 3. Conduramines and Inosamines 4. Pyrrolidine, and Piperidine Alkaloids 5. Indolizidine, and Pyrrolizidine Alkaloids 6. Tropane Alkaloids 7. Tabtoxin and Tabtoxinine-ß-Lactam 8. Antitumor FR 900482 and Mitomycin K 9. Lycoricidine 10. Chiral Amino Acids 11. Conclusion and Outlook