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Intramolecular Diels–Alder reaction leading to tricyclic derivatives as intermediates of natural products synthesis

✍ Scribed by Junichi Shiina; Shigeru Nishiyama

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
176 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

Tricyclic compounds 4a and 4b possessing a bicyclo[4.3.0] moiety, were successfully synthesized by using the intramolecular Diels -Alder reaction. The siloxy-rather than acyloxy-substituents increased the ratio of the endo-cylcoadducts 10 and 12. The oxygen substitution of 9 influenced conformation of the transition state, which was stereochemically restricted by the butenolide moiety. In addition, 9b carrying a hydroxyl group also produced 10b in a similar ratio to 9a. Compound 11 was the only exo-adduct produced in all of the entries.

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Mechanism leading to the observed produc
Mechanism leading to the observed product of intramolecular aryl Diels–Alder reaction
✍ Samuel Chackalamannil; Darı́o Doller; Keith Eagen 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 75 KB

A mechanistic investigation into the recently reported intramolecular aryl Diels-Alder reaction was carried out using deuterium labeling. These studies led to the conclusion that the initial Diels-Alder adduct is isomerized to a highly conjugated tetra-ene intermediate which undergoes a stereospecif