Design and synthesis of oxa-bowls via Diels–Alder reaction and ring-rearrangement metathesis as key steps

• Published in: Tetrahedron letters Vol. 55; no. 42; pp. 5781 - 5784
• Main Authors: Kotha, Sambasivarao, Ravikumar, Ongolu
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 15-10-2014
• Subjects: Norbornene derivatives; Oxa-bowls; Polycyclics; Ring-rearrangement metathesis; Polycyclics; Ring-rearrangement metathesis; Oxa-bowls; Norbornene derivatives
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2014.08.108

•Diels–Alder (DA) reaction is useful to design ring-rearrangement metathesis precursors.•Norbornene derivatives prepared by DA reaction undergo ring-rearrangement metathesis.•Oxa-bowls containing dienes are generated by ring-rearrangement enyne metathesis.•Highly atom economic reactions are used to generate oxa-bowls.•Green chemistry has been used to generate oxa-bowls.
Ring-rearrangement metathesis of norbornene derivatives prepared by Diels–Alder reaction has been used to design various oxa-bowls. Enyne ring-rearrangement metathesis of norbornene ring systems with propargyl moiety produced diene containing oxa-bowls, suitable for further expansion by Diels–Alder strategy.