Diels−Alder Cycloaddition Approach to Puupehenone-Related Metabolites:  Synthesis of the Potent Angiogenesis Inhibitor 8-Epipuupehedione

• Published in: Journal of organic chemistry Vol. 72; no. 9; pp. 3332 - 3339
• Main Authors: Alvarez-Manzaneda, E. J, Chahboun, R, Cabrera, E, Alvarez, E, Haidour, A, Ramos, J. M, Alvarez-Manzaneda, R, Hmamouchi, M, Bouanou, H
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 27-04-2007
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Angiogenesis Inhibitors - chemical synthesis; Angiogenesis Inhibitors - chemistry; Chemistry; Chemistry, Organic - methods; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Sesquiterpenes - chemistry; Sesquiterpenes - metabolism; Terpenes - chemical synthesis; Terpenes - chemistry; Terpenoids; Xanthenes - chemical synthesis; Xanthones - chemistry; Xanthones - metabolism; Terpenoid; Cycloaddition; Terpene; Metabolite; Diterpene; Diels Alder addition; Oxygen heterocycle; Labdane derivatives; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0626663

A new synthetic strategy toward puupehenone-related bioactive metabolites from sclareol oxide, based on a Diels−Alder cycloaddition approach, is described. Utilizing this, marine ent-chromazonarol and the potent angiogenesis inhibitor 8-epipuupehedione have been synthesized.