Studies On Efficient Syntheses Of Cyclopenta[b]naphthalenes Derivatives Via Intramolecular Diels–Alder Reaction

Cyclopenta[b]naphthalene motif exists in Zeylanone, Kinamycin and Prodan derivatives that have important physiological activity compounds. Therefore the efficient synthesis of this structural unit has attracted the attention of synthetic chemists and medicinal chemists.Diels-Alder reaction has become one of the most important methods for the construction of six-membered-rings in organic synthesis. In recent years, great attention has been paid to the intramolecular Diels-Alder reaction, which can effectively synthesize lots of interesting fused- and bridged compounds, including a variety of natural products.We developed a concise and efficient synthetic pathway for the construction of multiple substituted cyclopenta[b]naphthalene derivatives through an intramolecular Diels-Alder reaction of α,α-dialkenoyl ketene dithioacetal. In this reaction, styrene unit is used as the dienes and alkene as the dienophile. This new method also has the advantages of high yield and high atom-economy.